Pyridazinone derivatives, and insecticidal, acaricidal and nematicidal compositions

ABSTRACT

Compounds of the following formula: ##STR1## wherein Z 3  represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR2## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is 0 or an integer of 1 to 2, and when m is 2, W may be same or different, and compositions for controlling insects, acari and nemati which contain such compound.

This is a continuation-in-part application of Ser. No. 008,359 filed Jan. 29, 1987 (now abandoned).

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to novel 3(2H)-pyridazinone derivatives; preparation thereof; insecticidal, acaricidal, and nematicidal compositions for agricultural and horticultural uses; and expellent compositions for ticks parasitic on animals; said compositions containing said derivatives as an active ingredient.

2. Description of the Prior Art

The present invention concerns EP-A-0088384, EP-A-0134439, EP-A-0183212 and EP-A-0199281. The known compounds contained in these patent applications are represented by the general formula (IV): ##STR3##

The characteristics of the compounds of these patent applications are, e.g., in the formula (IV):

in case of EP-A-0088384 and EP-A-0134439, Y represents oxygen atom or sulfur atom, but benzyl derivative group is bound thereto as -B'-Q';

in case of EP-A-0183212, A' represents alkyl group or it has double bond or triple bond as B';

in case of EP-A-0199281, Q' represents heterocyclic ring or specific substituent.

The present inventors have intensively conducted research on pyridazinone derivatives which are different from these EPC patent applications in chemical structure and have obtained the present compounds of the general formula (I) given below.

Furthermore, the present inventors have found out that the present compounds of the general formula (I) given below have excellent effective insecticidal, acaricidal and nematicidal activities.

For example, the group of known compounds represented by the aforesaid general formula (IV) have strong insecticidal, acaricidal and nematicidal activities. Even in comparison with those known compounds, however, the present compounds exhibited remarkable activity rise in respect to residual activity, especially for insecticidal and acaricidal activity. Therefore, the present invention was completed by finding out that the present compounds can effectively control pests which are agriculturally and horticulturally harmful even with an extremely low drug concentration in comparison with the known compounds represented by the general formula (IV).

SUMMARY OF THE INVENTION

An object of this invention is to provide novel 3(2H)-pyridazinone derivatives which have insecticidal, acaricidal and nematicidal activities.

Another object of this invention is to provide a process for preparing such 3(2H)-pyridazinone derivatives.

Further object of this invention is to provide insecticidal, acaricidal and nematicidal compositions containing 3(2H)-pyridazinone derivatives as an active ingredient.

Still further object of this invention is to provide a method for controlling pests by using the above-mentioned derivatives or compositions.

Other objects of this invention will become apparent from the description given below.

DETAILED DESCRIPTION OF THE INVENTION

The pyridazinone derivatives according to the invention have the general formula (I): ##STR4## wherein

R represents a straight or branched chain alkyl group having 2 to 6 carbon atoms,

A represents halogen atom,

X represents oxygen atom or sulfur atom,

Y represents oxygen atom, sulfur atom, or CH₂,

R¹ represents hydrogen atom or alkyl having 1 to 4 carbon atoms, Z¹ and Z⁴ represent independently hydrogen atom, alkyl group having 1 to 4 carbon atoms, halogen atom, alkoxy group having 1 to 4 carbon atoms or nitro group, with the proviso that when X represents oxygen atom, Z¹ and Z⁴ do not represent hydrogen atom; Z² represents hydrogen atom, alkyl group having 1 to 4 carbon atoms or alkoxy group having 1 to 4 carbon atoms;

Z³ represents hydrogen atom, halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, straight or branched chain alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, alkylsulfinyl group having 1 to 10 carbon atoms, alkylsulfonyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, haloalkyloxy group having 1 to 5 carbon atoms, alkylcarbonyl amino group having 2 to 5 carbon atoms, nitro group, alkylcarbonyl group having 1 to 10 carbon atoms, napthylcarbonyl group, --COCH₂ C₆ H₅ group, 2-phenylethyl group, hydroxyalkyl group having 1 to 4 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, alkylthioalkyl group having 2 to 4 carbon atoms, alkoxyiminoalkyl group having 2 to 4 carbon atoms, --NHSO₂ CH₃ group, --NHCON(CH₃)₂ group, ##STR5## group, cycloalkylcarbonyl group having 4 to 7 carbon atoms or cycloalkylmethyl group having 4 to 7 carbon atoms, ##STR6## provided that l represents 0 or an integer of 1 to 2, R⁸ represents hydrogen atom, alkyl group having 1 to 4 carbon atoms or alkylcarbonyl group having 1 to 4 carbon atoms, R⁹ to R¹⁰ represent independently hydrogen atom, alkyl group having 1 to 4 carbon atoms, halogen atom, or alkoxy group having 1 to 4 carbon atoms,

W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group,

m is 0 or an integer of 1 to 2, and when m is 2, W may be same or different, with the proviso that Z¹, Z², Z³ and Z⁴ do not simultaneously represent hydrogen atom.

In respect to the activity for controlling pests, preferable compounds of the present invention are ones in which, in the general formula (I), R represents t-Bu, A represents chlorine atom, R¹ represents hydrogen atom, and Y represents oxygen atom.

More preferred compounds of the general formula (I) among the compounds shown in Tables 1 to 3 are:

    ______________________________________                                         Nos.    36, 38, 40, 46, 49, 55, 71, 72, 73, 74, 84, 85,                                88, 89, 90, 92, 111, 112, 113, 127, 128, 129, 426,                             427, 429, 430, 432, 438, 443, 463, 465, 466, 468,                              470, 472, 474, 476, 477, 480, 481, 482, 484, 488,                              490, 491, 492, 494, 496, 514, 517, 518, 520, 522,                              524, 528, 540, 542, 850, 851, 852, 857, 863 and                                895.                                                                   ______________________________________                                    

The compounds shown in Tables 1, 2 and 3 are examples. However, the present invention is not restricted to these compounds which are shown as only exemplification.

In Tables 1, 2 and 3, t, i, c and s mean tertiary, iso, cyclo and secondary, respectively, and each symbol Me, Et, Pr, Bu, Am, Pen, Hex and Ph means methyl, ethyl, propyl, butyl, amyl, pentyl, hexyl and phenyl, respectively.

In case of the compounds containing asymmetric carbon atoms among the compounds covered by the present invention, optical isomers, i.e., (+)-isomers and (-)-isomers are also included in the present invention.

                                      TABLE 1                                      __________________________________________________________________________      ##STR7##                                                                      No. R   A   X  R.sup.1                                                                            Y   Z.sup.1                                                                            Z.sup.2                                                                            Z.sup.3    Z.sup.4                              __________________________________________________________________________     12  t-Bu                                                                               Cl  S  H   O   Me  H   H          H                                    13  t-Bu                                                                               Cl  S  H   O   H   H   Et         H                                    14  t-Bu                                                                               Cl  S  H   O   H   H   Pr         H                                    15  t-Bu                                                                               Cl  S  H   O   i-Pr                                                                               H   H          H                                    16  t-Bu                                                                               Cl  S  H   O   H   H   Bu         H                                    17  t-Bu                                                                               Cl  S  H   O   H   H   Pen        H                                    18  t-Bu                                                                               Cl  S  H   O   H   OPr H          H                                    19  t-Bu                                                                               Cl  S  H   O   H   H   OBu        H                                    20  t-Bu                                                                               Cl  S  H   O   H   H   SMe        H                                    21  t-Bu                                                                               Cl  S  H   O   Me  H   Cl         H                                    22  t-Bu                                                                               Cl  S  H   O   Me  H   Me         H                                    23  t-Bu                                                                               Cl  S  H   O   H   Me  H          Me                                   24  t-Bu                                                                               Cl  S  H   O   Me  H   H          Me                                   25  t-Bu                                                                               Cl  S  H   O   Me  H   Pen        H                                    26  t-Bu                                                                               Cl  S  H   O   Et  H   Pen        H                                    27  t-Bu                                                                               Cl  S  H   O   Me  H   CO(CH.sub.2).sub.3 CH.sub.3                                                               H                                    28  t-Bu                                                                               Cl  S  H   O   OMe H   H          OMe                                  29  t-Bu                                                                               Cl  S  H   O   Me  H   H          Cl                                   30  t-Bu                                                                               Cl  S  H   O   Cl  H   H          Cl                                   31  t-Bu                                                                               Cl  S  H   O   Me  H   Cl         Cl                                   32  t-Bu                                                                               Cl  S  H   O   Me  Me  H          Me                                   33  t-Bu                                                                               Cl  S  H   O   Me  H   Me         Me                                   34  t-Bu                                                                               Cl  S  H   O   Me  H   Br         Cl                                   35  t-Bu                                                                               Cl  S  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Cl                                   36  t-Bu                                                                               Cl  S  H   O   Me  H   Pr         Cl                                   37  t-Bu                                                                               Cl  S  H   O   Me  H   Bu         Cl                                   38  t-Bu                                                                               Cl  S  H   O   Cl  H   COCH.sub.2 CH.sub.3                                                                       Cl                                   39  t-Bu                                                                               Cl  S  H   O   Cl  H   Et         Cl                                   40  t-Bu                                                                               Cl  S  H   O   Cl  H   Pr         Cl                                   41  t-Bu                                                                               Cl  S  H   O   Cl  H   i-Pr       Cl                                   42  t-Bu                                                                               Cl  S  H   O   Cl  H   Bu         Cl                                   43  t-Bu                                                                               Cl  S  H   O   Cl  H   i-Bu       Cl                                   44  t-Bu                                                                               Cl  S  H   O   Cl  H   t-Bu       Cl                                   45  t-Bu                                                                               Cl  S  H   O   Cl  H   Pen        Cl                                   46  t-Bu                                                                               Cl  S  H   O   Cl  H   Ph         Cl                                   47  t-Bu                                                                               Cl  S  H   O   Br  H   COCH.sub.2 CH.sub.3                                                                       Br                                   48  t-Bu                                                                               Cl  S  H   O   Br  H   Et         Br                                   49  t-Bu                                                                               Cl  S  H   O   Br  H   Pr         Br                                   50  t-Bu                                                                               Cl  S  H   O   Br  H   i-Pr       Br                                   51  t-Bu                                                                               Cl  S  H   O   Br  H   Bu         Br                                   52  t-Bu                                                                               Cl  S  H   O   Br  H   i-Bu       Br                                   53  t-Bu                                                                               Cl  S  H   O   Br  H   t-Bu       Br                                   54  t-Bu                                                                               Cl  S  H   O   Br  H   Ph         Br                                   55  t-Bu                                                                               Cl  S  H   O   F   H   COCH.sub.2 CH.sub.3                                                                       F                                    56  t-Bu                                                                               Cl  S  H   O   F   H   CHCHCH.sub.3                                                                              F                                    57  t-Bu                                                                               Cl  S  H   O   F   H   Pr         F                                    58  t-Bu                                                                               Cl  S  H   O   F   H   Bu         F                                    59  t-Bu                                                                               Cl  S  H   O   F   H   Pen        F                                    60  t-Bu                                                                               Cl  S  H   O   F   H   Et         F                                    61  t-Bu                                                                               Cl  S  H   O   NO.sub.2                                                                           H   Me         NO.sub.2                             62  t-Bu                                                                               Cl  S  H   O   NO.sub.2                                                                           H   Et         NO.sub.2                             63  t-Bu                                                                               Cl  S  H   O   NO.sub.2                                                                           H   Pr         NO.sub.2                             64  t-Bu                                                                               Cl  S  H   O   NO.sub.2                                                                           H   Bu         NO.sub.2                             65  t-Bu                                                                               Cl  S  H   O   NO.sub.2                                                                           H   Pen        NO.sub.2                             66  t-Bu                                                                               Cl  S  H   O   OMe H   Et         OMe                                  67  t-Bu                                                                               Cl  S  H   O   OMe H   Pr         OMe                                  68  t-Bu                                                                               Cl  S  H   O   OMe H   i-Pr       OMe                                  69  t-Bu                                                                               Cl  S  H   O   OMe H   Bu         OMe                                  70  t-Bu                                                                               Cl  S  H   O   OMe H   t-Bu       OMe                                  71  t-Bu                                                                               Cl  S  H   O   Me  H   COCH.sub.3 Me                                   72  t-Bu                                                                               Cl  S  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   73  t-Bu                                                                               Cl  S  H   O   Me  H   COCH.sub.2 CH.sub.2 CH.sub.3                                                              Me                                   74  t-Bu                                                                               Cl  S  H   O   Me  H   COCH(CH.sub.3).sub.2                                                                      Me                                   75  t-Bu                                                                               Cl  S  H   O   Me  H   COc-Pr     Me                                   76  t-Bu                                                                               Cl  S  H   O   Me  H   CO(CH.sub.2).sub.3 CH.sub.3                                                               Me                                   77  t-Bu                                                                               Cl  S  H   O   Me  H   COc-Hex    Me                                   78  t-Bu                                                                               Cl  S  H   O   Me  H   CO(CH.sub.2).sub.4 CH.sub.3                                                               Me                                   79  t-Bu                                                                               Cl  S  H   O   Me  H   CO(CH.sub.2).sub.6 CH.sub.3                                                               Me                                   80  t-Bu                                                                               Cl  S  H   O   Me  H   CO(CH.sub.2).sub.8 CH.sub.3                                                               Me                                   81  t-Bu                                                                               Cl  S  H   O   Me  H   Cl         Me                                   82  t-Bu                                                                               Cl  S  H   O   Me  H   Br         Me                                   83  t-Bu                                                                               Cl  S  H   O   Me  H   I          Me                                   84  t-Bu                                                                               Cl  S  H   O   Me  H   Et         Me                                   85  t-Bu                                                                               Cl  S  H   O   Me  H   Pr         Me                                   86  t-Bu                                                                               Cl  S  H   O   Me  H   i-Pr       Me                                   87  t-Bu                                                                               Cl  S  H   O   Me  H   CH.sub.2 CHCH.sub.2                                                                       Me                                   88  t-Bu                                                                               Cl  S  H   O   Me  H   Bu         Me                                   89  t-Bu                                                                               Cl  S  H   O   Me  H   i-Bu       Me                                   90  t-Bu                                                                               Cl  S  H   O   Me  H   CH.sub.2c-Pr                                                                              Me                                   91  t-Bu                                                                               Cl  S  H   O   Me  H   CH.sub.2 CCH                                                                              Me                                   92  t-Bu                                                                               Cl  S  H   O   Me  H   t-Bu       Me                                   93  t-Bu                                                                               Cl  S  H   O   Me  H   Pen        Me                                   94  t-Bu                                                                               Cl  S  H   O   Me  H   t-Am       Me                                   95  t-Bu                                                                               Cl  S  H   O   Me  H   Hex        Me                                   96  t-Bu                                                                               Cl  S  H   O   Me  H   c-Hex      Me                                   97  t-Bu                                                                               Cl  S  H   O   Me  H   (CH.sub.2).sub.7 CH.sub.3                                                                 Me                                   98  t-Bu                                                                               Cl  S  H   O   Me  H   (CH.sub.2).sub.9 CH.sub.3                                                                 Me                                   99  t-Bu                                                                               Cl  S  H   O   Me  H   CH.sub.2c-Hex                                                                             Me                                   100 t-Bu                                                                               Cl  S  H   O   Me  H   Ph         Me                                   102 t-Bu                                                                               Cl  S  H   O   Me  H   NO.sub.2   Me                                   103 t-Bu                                                                               Cl  S  H   O   Me  H   COOMe      Me                                   104 t-Bu                                                                               Cl  S  H   O   Me  H   COOEt      Me                                   105 t-Bu                                                                               Cl  S  H   O   Me  H   COOPr      Me                                   106 t-Bu                                                                               Cl  S  H   O   Me  H   CH.sub.2 CF.sub.3                                                                         Me                                   107 t-Bu                                                                               Cl  S  H   O   Me  H   CH.sub.2 CH.sub.2 CF.sub.3                                                                Me                                   108 t-Bu                                                                               Cl  S  H   O   Me  H   NMe.sub.2  Me                                   109 t-Bu                                                                               Cl  S  H   O   Me  H   NEt.sub.2  Me                                   110 t-Bu                                                                               Cl  S  H   O   Me  H   NPr.sub.2  Me                                   111 t-Bu                                                                               Cl  S  H   O   Me  H   OMe        Me                                   112 t-Bu                                                                               Cl  S  H   O   Me  H   OEt        Me                                   113 t-Bu                                                                               Cl  S  H   O   Me  H   OPr        Me                                   114 t-Bu                                                                               Cl  S  H   O   Me  H   Oi-Pr      Me                                   115 t-Bu                                                                               Cl  S  H   O   Me  H   OBu        Me                                   116 t-Bu                                                                               Cl  S  H   O   Me  H   Ot-Bu      Me                                   117 t-Bu                                                                               Cl  S  H   O   Me  H   OPen       Me                                   118 t-Bu                                                                               Cl  S  H   O   Me  H   Oc-Hex     Me                                   119 t-Bu                                                                               Cl  S  H   O   Me  H   OCH.sub.2 CHCH.sub.2                                                                      Me                                   120 t-Bu                                                                               Cl  S  H   O   Me  H   OCH.sub.2 CCH                                                                             Me                                   121 t-Bu                                                                               Br  S  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   122 t-Bu                                                                               OMe S  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   123 t-Bu                                                                               SMe S  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   124 t-Bu                                                                               Br  S  H   O   Me  H   Pr         Me                                   125 t-Bu                                                                               OMe S  H   O   Me  H   Pr         Me                                   126 t-Bu                                                                               SMe S  H   O   Me  H   Pr         Me                                   127 t-Bu                                                                               Cl  S  H   O   Me  H   SMe        Me                                   128 t-Bu                                                                               Cl  S  H   O   Me  H   SEt        Me                                   129 t-Bu                                                                               Cl  S  H   O   Me  H   SPr        Me                                   130 t-Bu                                                                               Cl  S  H   O   Me  H   SOMe       Me                                   131 t-Bu                                                                               Cl  S  H   O   Me  H   SOEt       Me                                   132 t-Bu                                                                               Cl  S  H   O   Me  H   SOPr       Me                                   133 t-Bu                                                                               Cl  S  H   O   Me  H   SO.sub.2 Me                                                                               Me                                   134 t-Bu                                                                               Cl  S  H   O   Me  H   SO.sub.2 Et                                                                               Me                                   135 t-Bu                                                                               Cl  S  H   O   Me  H   SO.sub.2 Pr                                                                               Me                                   136 t-Bu                                                                               Cl  S  H   O   Me  H   SCH.sub.2 CHCH.sub.2                                                                      Me                                   137 t-Bu                                                                               Cl  S  H   O   Me  H   SCH.sub.2 CCH                                                                             Me                                   138 t-Bu                                                                               Cl  S  H   O   Me  H   SOCH.sub.2 CHCH.sub.2                                                                     Me                                   139 t-Bu                                                                               Cl  S  H   O   Me  H   SOCH.sub.2 CCH                                                                            Me                                   140 t-Bu                                                                               Cl  S  H   O   Me  H   SO.sub.2 CH.sub.2 CHCH.sub.2                                                              Me                                   141 t-Bu                                                                               Cl  S  H   O   Me  H   SO.sub.2 CH.sub.2 CCH                                                                     Me                                   142 t-Bu                                                                               Cl  S  H   O   Me  H   Si-Pr      Me                                   143 t-Bu                                                                               Cl  S  H   O   Me  H   St-Br      Me                                   144 t-Bu                                                                               Cl  S  H   O   Me  H   Sc-Hex     Me                                   145 t-Bu                                                                               Cl  S  H   O   Me  H   SO.sub.2i-Pr                                                                              Me                                   146 t-Bu                                                                               Cl  S  H   O   Me  H   SO.sub.2t-Bu                                                                              Me                                   147 t-Bu                                                                               Cl  S  H   O   Me  H   SOc-Hex    Me                                   148 t-Bu                                                                               Cl  S  H   O   Cl  Et  Cl         Cl                                   149 t-Bu                                                                               Cl  S  H   O   Cl  Pr  Cl         Cl                                   150 t-Bu                                                                               Cl  S  H   O   Cl  t-Bu                                                                               Cl         Cl                                   151 t-Bu                                                                               Cl  S  H   S   H   H   t-Bu       H                                    152 t-Bu                                                                               Cl  S  H   S   Me  H   H          Me                                   153 t-Bu                                                                               Cl  S  H   S   Me  H   Me         Me                                   154 t-Bu                                                                               Cl  S  H   S   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   155 t-Bu                                                                               Cl  S  H   S   Me  H   Pr         Me                                   156 t-Bu                                                                               Cl  S  H   S   Me  H   OEt        Me                                   161 t-Bu                                                                               Cl  S  H   CH.sub.2                                                                           H   H   t-Bu       H                                    162 t-Bu                                                                               Cl  S  H   CH.sub.2                                                                           Me  H   H          Me                                   163 t-Bu                                                                               Cl  S  H   CH.sub.2                                                                           Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   164 t-Bu                                                                               Cl  S  H   CH.sub.2                                                                           Me  H   Pr         Me                                   165 t-Bu                                                                               Cl  S  H   CH.sub.2                                                                           Me  H   OEt        Me                                   171 t-Bu                                                                               Cl  S  Me  O   H   H   t-Bu       H                                    172 t-Bu                                                                               Cl  S  Me  O   Me  H   H          Me                                   173 t-Bu                                                                               Cl  S  Me  O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   174 t-Bu                                                                               Cl  S  Me  O   Me  H   Pr         Me                                   175 t-Bu                                                                               Cl  S  Me  O   Me  H   OEt        Me                                   198 t-Bu                                                                               Cl  O  H   S   Me  H   H          Me                                   199 t-Bu                                                                               Cl  O  H   S   Me  H   Me         Me                                   219 t-Bu                                                                               Cl  O  H   O   Me  H   H          Me                                   223 t-Bu                                                                               Cl  O  H   O   OMe H   H          OMe                                  224 t-Bu                                                                               Cl  O  H   O   Me  H   H          Cl                                   225 t-Bu                                                                               Cl  O  H   O   Cl  H   H          Cl                                   226 t-Bu                                                                               Cl  O  H   O   Me  H   Cl         Cl                                   227 Pr  Cl  O  H   O   Me  H   Cl         Cl                                   228 t-Bu                                                                               Cl  O  H   O   Me  Me  H          Me                                   229 t-Bu                                                                               Cl  O  H   O   Me  H   Me         Me                                   230 t-Bu                                                                               Cl  O  H   O   Me  H   Br         Cl                                   231 t-Bu                                                                               Cl  O  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Cl                                   232 t-Bu                                                                               Cl  O  H   O   Me  H   Pr         Cl                                   233 t-Bu                                                                               Cl  O  H   O   Cl  H   COCH.sub.2 CH.sub.3                                                                       Cl                                   234 t-Bu                                                                               Cl  O  H   O   Cl  H   Et         Cl                                   235 t-Bu                                                                               Cl  O  H   O   Cl  H   Pr         Cl                                   236 t-Bu                                                                               Cl  O  H   O   Cl  H   i-Pr       Cl                                   237 t-Bu                                                                               Cl  O  H   O   Cl  H   Bu         Cl                                   238 t-Bu                                                                               Cl  O  H   O   Cl  H   i-Bu       Cl                                   239 t-Bu                                                                               Cl  O  H   O   Cl  H   t-Bu       Cl                                   240 t-Bu                                                                               Cl  O  H   O   Cl  H   Pen        Cl                                   241 t-Bu                                                                               Cl  O  H   O   Cl  H   Ph         Cl                                   242 t-Bu                                                                               Cl  O  H   O   Br  H   COCH.sub.2 CH.sub.3                                                                       Br                                   243 t-Bu                                                                               Cl  O  H   O   Br  H   Et         Br                                   244 t-Bu                                                                               Cl  O  H   O   Br  H   Pr         Br                                   245 t-Bu                                                                               Cl  O  H   O   Br  H   i-Pr       Br                                   246 t-Bu                                                                               Cl  O  H   O   Br  H   Bu         Br                                   247 t-Bu                                                                               Cl  O  H   O   Br  H   i-Bu       Br                                   248 t-Bu                                                                               Cl  O  H   O   Br  H   t-Bu       Br                                   249 t-Bu                                                                               Cl  O  H   O   Br  H   Ph         Br                                   250 t-Bu                                                                               Cl  O  H   O   F   H   COCH.sub.2 CH.sub.3                                                                       F                                    251 t-Bu                                                                               Cl  O  H   O   F   H   CHCHCH.sub.3                                                                              F                                    252 t-Bu                                                                               Cl  O  H   O   F   H   Pr         F                                    253 t-Bu                                                                               Cl  O  H   O   F   H   Bu         F                                    254 t-Bu                                                                               Cl  O  H   O   F   H   Pen        F                                    255 t-Bu                                                                               Cl  O  H   O   F   H   Et         F                                    256 t-Bu                                                                               Cl  O  H   O   NO.sub.2                                                                           H   Me         NO.sub.2                             257 t-Bu                                                                               Cl  O  H   O   NO.sub.2                                                                           H   Et         NO.sub.2                             258 t-Bu                                                                               Cl  O  H   O   NO.sub.2                                                                           H   Pr         NO.sub.2                             259 t-Bu                                                                               Cl  O  H   O   NO.sub.2                                                                           H   Bu         NO.sub.2                             260 t-Bu                                                                               Cl  O  H   O   NO.sub.2                                                                           H   Pen        NO.sub.2                             261 t-Bu                                                                               Cl  O  H   O   OMe H   Et         OMe                                  262 t-Bu                                                                               Cl  O  H   O   OMe H   Pr         OMe                                  263 t-Bu                                                                               Cl  O  H   O   OMe H   i-Pr       OMe                                  264 t-Bu                                                                               Cl  O  H   O   OMe H   Bu         OMe                                  265 t-Bu                                                                               Cl  O  H   O   OMe H   t-Bu       OMe                                  266 t-Bu                                                                               Cl  O  H   O   Me  H   COCH.sub.3 Me                                   267 t-Bu                                                                               Cl  O  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   268 t-Bu                                                                               Cl  O  H   O   Me  H   COCH.sub.2 CH.sub.2 CH.sub.3                                                              Me                                   269 t-Bu                                                                               Cl  O  H   O   Me  H   COCH(CH.sub.3).sub.2                                                                      Me                                   270 t-Bu                                                                               Cl  O  H   O   Me  H   COc-Pr     Me                                   271 t-Bu                                                                               Cl  O  H   O   Me  H   CO(CH.sub.2).sub.3 CH.sub.3                                                               Me                                   272 t-Bu                                                                               Cl  O  H   O   Me  H   COc-Hex    Me                                   273 t-Bu                                                                               Cl  O  H   O   Me  H   CO(CH.sub.2).sub.4 CH.sub.3                                                               Me                                   274 t-Bu                                                                               Cl  O  H   O   Me  H   CO(CH.sub.2).sub.6 CH.sub.3                                                               Me                                   275 t-Bu                                                                               Cl  O  H   O   Me  H   CO(CH.sub.3).sub.8 CH.sub.3                                                               Me                                   276 t-Bu                                                                               Cl  O  H   O   Me  H   Cl         Me                                   277 t-Bu                                                                               Cl  O  H   O   Me  H   Br         Me                                   278 t-Bu                                                                               Cl  O  H   O   Me  H   I          Me                                   279 t-Bu                                                                               Cl  O  H   O   Me  H   Et         Me                                   280 t-Bu                                                                               Cl  O  H   O   Me  H   Pr         Me                                   281 t-Bu                                                                               Cl  O  H   O   Me  H   i-Pr       Me                                   282 t-Bu                                                                               Cl  O  H   O   Me  H   CH.sub.2 CHCH.sub.2                                                                       Me                                   283 t-Bu                                                                               Cl  O  H   O   Me  H   Bu         Me                                   284 t-Bu                                                                               Cl  O  H   O   Me  H   i-Bu       Me                                   285 t-Bu                                                                               Cl  O  H   O   Me  H   CH.sub.2c-Pr                                                                              Me                                   286 t-Bu                                                                               Cl  O  H   O   Me  H   CH.sub.2 CCH                                                                              Me                                   287 t-Bu                                                                               Cl  O  H   O   Me  H   t-Bu       Me                                   288 t-Bu                                                                               Cl  O  H   O   Me  H   Pen        Me                                   289 t-Bu                                                                               Cl  O  H   O   Me  H   t-Am       Me                                   290 t-Bu                                                                               Cl  O  H   O   Me  H   Hex        Me                                   291 t-Bu                                                                               Cl  O  H   O   Me  H   c-Hex      Me                                   292 t-Bu                                                                               Cl  O  H   O   Me  H   (CH.sub.2).sub.7 CH.sub.3                                                                 Me                                   293 t-Bu                                                                               Cl  O  H   O   Me  H   (CH.sub.2).sub.9 CH.sub.3                                                                 Me                                   294 t-Bu                                                                               Cl  O  H   O   Me  H   CH.sub.2c-Hex                                                                             Me                                   295 t-Bu                                                                               Cl  O  H   O   Me  H   Ph         Me                                   296 t-Bu                                                                               Cl  O  H   O   Me  H   NO.sub.2   Me                                   298 t-Bu                                                                               Cl  O  H   O   Me  H   COOMe      Me                                   299 t-Bu                                                                               Cl  O  H   O   Me  H   COOEt      Me                                   300 t-Bu                                                                               Cl  O  H   O   Me  H   COOPr      Me                                   301 t-Bu                                                                               Cl  O  H   O   Me  H   CH.sub.2 CF.sub.3                                                                         Me                                   302 t-Bu                                                                               Cl  O  H   O   Me  H   CH.sub.2 CH.sub.2 CF.sub.3                                                                Me                                   303 t-Bu                                                                               Cl  O  H   O   Me  H   NMe.sub.2  Me                                   304 t-Bu                                                                               Cl  O  H   O   Me  H   NEt.sub.2  Me                                   305 t-Bu                                                                               Cl  O  H   O   Me  H   NPr.sub.2  Me                                   306 t-Bu                                                                               Cl  O  H   O   Me  H   OMe        Me                                   307 t-Bu                                                                               Cl  O  H   O   Me  H   OEt        Me                                   308 t-Bu                                                                               Cl  O  H   O   Me  H   OPr        Me                                   309 t-Bu                                                                               Cl  O  H   O   Me  H   Oi-Pr      Me                                   310 t-Bu                                                                               Cl  O  H   O   Me  H   OBu        Me                                   311 t-Bu                                                                               Cl  O  H   O   Me  H   Ot-Bu      Me                                   312 t-Bu                                                                               Cl  O  H   O   Me  H   OPen       Me                                   313 t-Bu                                                                               Cl  O  H   O   Me  H   Oc-Hex     Me                                   314 t-Bu                                                                               Cl  O  H   O   Me  H   OCH.sub.2 CHCH.sub.2                                                                      Me                                   315 t-Bu                                                                               Cl  O  H   O   Me  H   OCH.sub.2 CCH.sub.3                                                                       Me                                   316 t-Bu                                                                               Br  O  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   317 t-Bu                                                                               OMe O  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   318 t-Bu                                                                               SMe O  H   O   Me  H   COCH.sub.2 CH.sub.3                                                                       Me                                   319 t-Bu                                                                               Br  O  H   O   Me  H   Pr         Me                                   320 t-Bu                                                                               OMe O  H   O   Me  H   Pr         Me                                   321 t-Bu                                                                               SMe O  H   O   Me  H   Pr         Me                                   322 t-Bu                                                                               Cl  O  H   O   Me  H   SMe        Me                                   323 t-Bu                                                                               Cl  O  H   O   Me  H   SEt        Me                                   324 t-Bu                                                                               Cl  O  H   O   Me  H   SPr        Me                                   325 t-Bu                                                                               Cl  O  H   O   Me  H   SOMe       Me                                   326 t-Bu                                                                               Cl  O  H   O   Me  H   SOEt       Me                                   327 t-Bu                                                                               Cl  O  H   O   Me  H   SOPr       Me                                   328 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2 Me                                                                               Me                                   329 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2 Et                                                                               Me                                   330 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2 Pr                                                                               Me                                   331 t-Bu                                                                               Cl  O  H   O   Me  H   SCH.sub.2 CHCH.sub.2                                                                      Me                                   332 t-Bu                                                                               Cl  O  H   O   Me  H   SCH.sub.2 CCH.sub.3                                                                       Me                                   333 t-Bu                                                                               Cl  O  H   O   Me  H   SOCH.sub.2 CHCH.sub.2                                                                     Me                                   334 t-Bu                                                                               Cl  O  H   O   Me  H   SOCH.sub.2 CCH.sub.3                                                                      Me                                   335 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2 CH.sub.2 CHCH.sub.2                                                              Me                                   336 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2 CH.sub.2 C CH.sub.3                                                              Me                                   337 t-Bu                                                                               Cl  O  H   O   Me  H   Si-Pr      Me                                   338 t-Bu                                                                               Cl  O  H   O   Me  H   St-Bu      Me                                   339 t-Bu                                                                               Cl  O  H   O   Me  H   Sc-Hex     Me                                   340 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2i-Pr                                                                              Me                                   341 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2t-Bu                                                                              Me                                   342 t-Bu                                                                               Cl  O  H   O   Me  H   SO.sub.2c-Hex                                                                             Me                                   343 t-Bu                                                                               Cl  O  H   O   Cl  Et  Cl         Cl                                   344 t-Bu                                                                               Cl  O  H   O   Cl  t-Bu                                                                               Cl         Cl                                   360 t-Bu                                                                               Cl  O  Me  O   Me  H   Pr         Me                                   __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR8##                                                                      No.                                                                               R  A  X R.sup.1                                                                           Y Z.sup.5                                                                           Q    Z.sup.6.sub.n                                          __________________________________________________________________________     421                                                                               t-Bu                                                                              Cl S H  O H  O    H                                                      422                                                                               t-Bu                                                                              Cl S H  O H  O    4-Cl                                                   423                                                                               t-Bu                                                                              Cl S H  O H  O    4-Me                                                   424                                                                               t-Bu                                                                              Cl S H  O Cl O    H                                                      425                                                                               t-Bu                                                                              Cl S H  O Cl O    4-Me                                                   426                                                                               t-Bu                                                                              Cl S H  O Me O    H                                                      427                                                                               t-Bu                                                                              Cl S H  O Me O    4-Cl                                                   428                                                                               t-Bu                                                                              Cl S H  O Me O    2-Me                                                   429                                                                               t-Bu                                                                              Cl S H  O Me O    4-Me                                                   430                                                                               t-Bu                                                                              Cl S H  O Me O    4-Et                                                   431                                                                               t-Bu                                                                              Cl S H  O Me O    4-t-Bu                                                 432                                                                               t-Bu                                                                              Cl S H  O Me O    4-OMe                                                  433                                                                               t-Bu                                                                              Cl S H  O Me O    4-CF.sub.3                                             434                                                                               t-Bu                                                                              Cl S H  O Me O    4-NO.sub.2                                             435                                                                               t-Bu                                                                              Cl S H  O Me O    4-CN                                                   436                                                                               t-Bu                                                                              Cl S H  O Me O    4-OCF.sub.3                                            437                                                                               t-Bu                                                                              Cl S H  O Me O    2-Cl,4-Cl                                              438                                                                               t-Bu                                                                              Cl S H  O Me O    2-Me,4-Me                                              439                                                                               t-Bu                                                                              Cl S H  O Me O    2-Cl,4-Cl,6-Cl                                         440                                                                               t-Bu                                                                              Cl S H  O Me O    2-Me,4-Me,6-Me                                         441                                                                               t-Bu                                                                              Cl S H  O H  S    H                                                      442                                                                               t-Bu                                                                              Cl S H  O H  S    4-Me                                                   443                                                                               t-Bu                                                                              Cl S H  O Me S    H                                                      444                                                                               t-Bu                                                                              Cl S H  O Me S    4-F                                                    445                                                                               t-Bu                                                                              Cl S H  O Me S    4-Cl                                                   446                                                                               t-Bu                                                                              Cl S H  O Me SO   4-Cl                                                   447                                                                               t-Bu                                                                              Cl S H  O Me SO.sub.2                                                                            4-Cl                                                   448                                                                               t-Bu                                                                              Cl S H  O Me S    4-Me                                                   449                                                                               t-Bu                                                                              Cl S H  O Me SO   4-Me                                                   450                                                                               t-Bu                                                                              Cl S H  O Me SO.sub.2                                                                            4-Me                                                   451                                                                               t-Bu                                                                              Cl S H  O H  NH   H                                                      452                                                                               t-Bu                                                                              Cl S H  O H  NH   4-Cl                                                   453                                                                               t-Bu                                                                              Cl S H  O Me NH   H                                                      454                                                                               t-Bu                                                                              Cl S H  O Me NH   4-Cl                                                   455                                                                               t-Bu                                                                              Cl S H  O Me NMe  H                                                      456                                                                               t-Bu                                                                              Cl S H  O Me NMe  4-Cl                                                   457                                                                               t-Bu                                                                              Cl S H  O Me NCOMe                                                                               H                                                      458                                                                               t-Bu                                                                              Cl S H  O Me NCOMe                                                                               4-Cl                                                   459                                                                               t-Bu                                                                              Cl S H  O H  CO   H                                                      460                                                                               t-Bu                                                                              Cl S H  O H  CO   4-Cl                                                   461                                                                               t-Bu                                                                              Cl S H  O H  CO   4-Me                                                   462                                                                               t-Bu                                                                              Cl S H  O Cl CO   H                                                      463                                                                               t-Bu                                                                              Cl S H  O Cl CO   4-Cl                                                   464                                                                               t-Bu                                                                              Cl S H  O Cl CO   4-Me                                                   465                                                                               t-Bu                                                                              Cl S H  O Me CO   H                                                      466                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Cl                                                   467                                                                               t-Bu                                                                              Cl S H  O Me CO   3-Cl                                                   468                                                                               t-Bu                                                                              Cl S H  O Me CO   4-Cl                                                   469                                                                               t-Bu                                                                              Cl S H  O Me CO   2-F                                                    470                                                                               t-Bu                                                                              Cl S H  O Me CO   4-F                                                    471                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Br                                                   472                                                                               t-Bu                                                                              Cl S H  O Me CO   4-Br                                                   473                                                                               t-Bu                                                                              Cl S H  O Me CO   4-I                                                    474                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Me                                                   475                                                                               t-Bu                                                                              Cl S H  O Me CO   3-Me                                                   476                                                                               t-Bu                                                                              Cl S H  O Me CO   4-Me                                                   477                                                                               t-Bu                                                                              Cl S H  O Me CO   4-Et                                                   478                                                                               t-Bu                                                                              Cl S H  O Me CO   4-Bu                                                   479                                                                               t-Bu                                                                              Cl S H  O Me CO   4-i-Pr                                                 480                                                                               t-Bu                                                                              Cl S H  O Me CO   4-t-Bu                                                 481                                                                               t-Bu                                                                              Cl S H  O Me CO   4-CF.sub.3                                             482                                                                               t-Bu                                                                              Cl S H  O Me CO   4-NO.sub.2                                             483                                                                               t-Bu                                                                              Cl S H  O Me CO   4-CN                                                   484                                                                               t-Bu                                                                              Cl S H  O Me CO   4-OMe                                                  485                                                                               t-Bu                                                                              Cl S H  O Me CO   4-OEt                                                  486                                                                               t-Bu                                                                              Cl S H  O Me CO   4-SMe                                                  487                                                                               t-Bu                                                                              Cl S H  O Me CO   4-NMe.sub.2                                            488                                                                               t-Bu                                                                              Cl S H  O Me CO   2-F,4-F                                                489                                                                               t-Bu                                                                              Cl S H  O Me CO   2-F,6-F                                                490                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Cl,4-Cl                                              491                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Cl,6-Cl                                              492                                                                               t-Bu                                                                              Cl S H  O Me CO   3-Cl,4-Cl                                              493                                                                               t-Bu                                                                              Cl S H  O Me CO   3-Cl,5-Cl                                              494                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Cl,4-NO.sub.2                                        495                                                                               t-Bu                                                                              Cl S H  O Me CO   2-NO.sub.2,4-Cl                                        496                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Me,4-Me                                              497                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Me,6-Me                                              498                                                                               t-Bu                                                                              Cl S H  O Me CO   3-Me,4-Me                                              499                                                                               t-Bu                                                                              Cl S H  O Me CO   3-Me,5-Me                                              500                                                                               t-Bu                                                                              Cl S H  O Me CO   3,4-CHCHCHCH                                           501                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Cl,4-Me                                              502                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Cl,6-Me                                              503                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Me,4-Cl                                              504                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Cl,4-Cl,6-Cl                                         505                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Me,4-Me,5-Me                                         506                                                                               t-Bu                                                                              Cl S H  O Me CO   2-Me,4-Me,6-Me                                         507                                                                               t-Bu                                                                              Br S H  O Me CO   H                                                      508                                                                               t-Bu                                                                              OMe                                                                               S H  O Me CO   H                                                      509                                                                               t-Bu                                                                              SMe                                                                               S H  O Me CO   H                                                      510                                                                               t-Bu                                                                              Cl S H  O i-Pr                                                                              CO   H                                                      511                                                                               t-Bu                                                                              Cl S H  O H  CH.sub.2                                                                            H                                                      512                                                                               t-Bu                                                                              Cl S H  O H  CH.sub.2                                                                            4-Cl                                                   513                                                                               t-Bu                                                                              Cl S H  O H  CH.sub.2                                                                            4-Me                                                   514                                                                               t-Bu                                                                              Cl S H  O Cl CH.sub.2                                                                            H                                                      515                                                                               t-Bu                                                                              Cl S H  O Cl CH.sub.2                                                                            4-Cl                                                   516                                                                               t-Bu                                                                              Cl S H  O Cl CH.sub.2                                                                            4-Me                                                   517                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            H                                                      518                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Cl                                                   619                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            3-Cl                                                   520                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-Cl                                                   521                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-F                                                    522                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-F                                                    523                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Br                                                   524                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-Br                                                   525                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-I                                                    526                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Me                                                   527                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            3-Me                                                   528                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-Me                                                   529                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-Et                                                   530                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-Bu                                                   531                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-i-Pr                                                 532                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-t-Bu                                                 533                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-CF.sub.3                                             534                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-NO.sub.2                                             535                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-CN                                                   536                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-OMe                                                  537                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-OEt                                                  538                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-SMe                                                  539                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            4-NMe.sub.2                                            540                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-F,4-F                                                541                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-F,6-F                                                542                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Cl,4-Cl                                              543                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Cl,6-Cl                                              544                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            3-Cl,4-Cl                                              545                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            3-Cl,5-Cl                                              546                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Cl,4-NO.sub.2                                        547                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-NO.sub.2,4-Cl                                        548                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Me,4-Me                                              549                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Me,6-Me                                              550                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            3-Me,4-Me                                              551                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            3-Me,5-Me                                              552                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            3,4-CHCHCHCH                                           553                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Cl,4-Me                                              554                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Cl,6-Me                                              555                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Me,4-Cl                                              556                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Cl,4-Cl,6-Cl                                         557                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Me,4-Me,5-Me                                         558                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2                                                                            2-Me,4-Me,6-Me                                         559                                                                               t-Bu                                                                              Br S H  O Me CH.sub.2                                                                            H                                                      560                                                                               t-Bu                                                                              OMe                                                                               S H  O Me CH.sub.2                                                                            H                                                      561                                                                               t-Bu                                                                              SMe                                                                               S H  O Me CH.sub.2                                                                            H                                                      562                                                                               t-Bu                                                                              Cl S H  O i-Pr                                                                              CH.sub.2                                                                            H                                                      563                                                                               t-Bu                                                                              Cl S H  O Me CHMe H                                                      564                                                                               t-Bu                                                                              Cl S H  O Me CHMe 4-Cl                                                   565                                                                               t-Bu                                                                              Cl S H  O Me CHMe 4-Me                                                   566                                                                               t-Bu                                                                              Cl S H  O Me CHMe 4-OMe                                                  567                                                                               t-Bu                                                                              Cl S H  O i-Pr                                                                              CHMe H                                                      568                                                                               t-Bu                                                                              Cl S H  O i-Pr                                                                              CHMe 4-Cl                                                   569                                                                               t-Bu                                                                              Cl S H  O i-Pr                                                                              CHMe 4-Me                                                   570                                                                               t-Bu                                                                              Cl S H  O i-Pr                                                                              CHMe 4-OMe                                                  575                                                                               t-Bu                                                                              Cl S H  O H  OCH.sub.2                                                                           H                                                      576                                                                               t-Bu                                                                              Cl S H  O H  OCH.sub.2                                                                           4-Cl                                                   577                                                                               t-Bu                                                                              Cl S H  O H  OCH.sub.2                                                                           4-Me                                                   578                                                                               t-Bu                                                                              Cl S H  O H  OCH.sub.2                                                                           4-OMe                                                  579                                                                               t-Bu                                                                              Cl S H  O H  COCH.sub.2                                                                          H                                                      583                                                                               t-Bu                                                                              Cl S H  O Cl COCH.sub.2                                                                          H                                                      587                                                                               t-Bu                                                                              Cl S H  O Br COCH.sub.2                                                                          H                                                      589                                                                               t-Bu                                                                              Cl S H  O Me COCH.sub.2                                                                          H                                                      593                                                                               t-Bu                                                                              Cl S H  O H  CH.sub.2 CH.sub.2                                                                   H                                                      597                                                                               t-Bu                                                                              Cl S H  O Me CH.sub.2 CH.sub.2                                                                   H                                                      604                                                                               t-Bu                                                                              Cl O H  O Cl O    H                                                      605                                                                               t-Bu                                                                              Cl O H  O Cl O    4-Me                                                   606                                                                               t-Bu                                                                              Cl O H  O Me O    H                                                      607                                                                               t-Bu                                                                              Cl O H  O Me O    4-Cl                                                   608                                                                               t-Bu                                                                              Cl O H  O Me O    2-Me                                                   609                                                                               t-Bu                                                                              Cl O H  O Me O    4-Me                                                   610                                                                               t-Bu                                                                              Cl O H  O Me O    4-Et                                                   611                                                                               t-Bu                                                                              Cl O H  O Me O    4-t-Bu                                                 612                                                                               t-Bu                                                                              Cl O H  O Me O    4-OMe                                                  613                                                                               t-Bu                                                                              Cl O H  O Me O    4-CF.sub.3                                             614                                                                               t-Bu                                                                              Cl O H  O Me O    4-NO.sub.2                                             615                                                                               t-Bu                                                                              Cl O H  O Me O    4-CN                                                   616                                                                               t-Bu                                                                              Cl O H  O Me O    4-OCF.sub.3                                            617                                                                               t-Bu                                                                              Cl O H  O Me O    2-Cl,4-Cl                                              618                                                                               t-Bu                                                                              Cl O H  O Me O    2-Me,4-Me                                              619                                                                               t-Bu                                                                              Cl O H  O Me O    2-Cl,4-Cl,6-Cl                                         620                                                                               t-Bu                                                                              Cl O H  O Me O    2-Me,4-Me,6-Me                                         623                                                                               t-Bu                                                                              Cl O H  O Me S    H                                                      624                                                                               t-Bu                                                                              Cl O H  O Me S    4-F                                                    625                                                                               t-Bu                                                                              Cl O H  O Me S    4-Cl                                                   626                                                                               t-Bu                                                                              Cl O H  O Me SO   4-Cl                                                   627                                                                               t-Bu                                                                              Cl O H  O Me SO.sub.2                                                                            4-Cl                                                   628                                                                               t-Bu                                                                              Cl O H  O Me S    4-Me                                                   629                                                                               t-Bu                                                                              Cl O H  O Me SO   4-Me                                                   630                                                                               t-Bu                                                                              Cl O H  O Me SO.sub.2                                                                            4-Me                                                   633                                                                               t-Bu                                                                              Cl O H  O Me NH   H                                                      634                                                                               t-Bu                                                                              Cl O H  O Me NH   4-Cl                                                   635                                                                               t-Bu                                                                              Cl O H  O Me NH   4-Me                                                   636                                                                               t-Bu                                                                              Cl O H  O Me NMe  H                                                      637                                                                               t-Bu                                                                              Cl O H  O Me NMe  4-Cl                                                   638                                                                               t-Bu                                                                              Cl O H  O Me NMe  4-Me                                                   642                                                                               t-Bu                                                                              Cl O H  O Cl CO   H                                                      643                                                                               t-Bu                                                                              Cl O H  O Cl CO   4-Cl                                                   644                                                                               t-Bu                                                                              Cl O H  O Cl CO   4-Me                                                   645                                                                               t-Bu                                                                              Cl O H  O Me CO   H                                                      646                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Cl                                                   647                                                                               t-Bu                                                                              Cl O H  O Me CO   3-Cl                                                   648                                                                               t-Bu                                                                              Cl O H  O Me CO   4-Cl                                                   649                                                                               t-Bu                                                                              Cl O H  O Me CO   2-F                                                    650                                                                               t-Bu                                                                              Cl O H  O Me CO   4-F                                                    651                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Br                                                   652                                                                               t-Bu                                                                              Cl O H  O Me CO   4-Br                                                   653                                                                               t-Bu                                                                              Cl O H  O Me CO   4-I                                                    654                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Me                                                   655                                                                               t-Bu                                                                              Cl O H  O Me CO   3-Me                                                   656                                                                               t-Bu                                                                              Cl O H  O Me CO   4-Me                                                   657                                                                               t-Bu                                                                              Cl O H  O Me CO   4-Et                                                   658                                                                               t-Bu                                                                              Cl O H  O Me CO   4-Bu                                                   659                                                                               t-Bu                                                                              Cl O H  O Me CO   4-i-Pr                                                 660                                                                               t-Bu                                                                              Cl O H  O Me CO   4-t-Bu                                                 661                                                                               t-Bu                                                                              Cl O H  O Me CO   4-CF.sub.3                                             662                                                                               t-Bu                                                                              Cl O H  O Me CO   4-NO.sub.2                                             663                                                                               t-Bu                                                                              Cl O H  O Me CO   4-CN                                                   664                                                                               t-Bu                                                                              Cl O H  O Me CO   4-OMe                                                  665                                                                               t-Bu                                                                              Cl O H  O Me CO   4-OEt                                                  666                                                                               t-Bu                                                                              Cl O H  O Me CO   4-SMe                                                  667                                                                               t-Bu                                                                              Cl O H  O Me CO   4-NMe.sub.2                                            668                                                                               t-Bu                                                                              Cl O H  O Me CO   2-F,4-F                                                669                                                                               t-Bu                                                                              Cl O H  O Me CO   2-F,6-F                                                670                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Cl,4-Cl                                              671                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Cl,6-Cl                                              672                                                                               t-Bu                                                                              Cl O H  O Me CO   3-Cl,4-Cl                                              673                                                                               t-Bu                                                                              Cl O H  O Me CO   3-Cl,5-Cl                                              674                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Cl,4-NO.sub.2                                        675                                                                               t-Bu                                                                              Cl O H  O Me CO   2-NO.sub.2,4-Cl                                        676                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Me,4-Me                                              677                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Me,6-Me                                              678                                                                               t-Bu                                                                              Cl O H  O Me CO   3-Me,4-Me                                              679                                                                               t-Bu                                                                              Cl O H  O Me CO   3-Me,5-Me                                              680                                                                               t-Bu                                                                              Cl O H  O Me CO   3,4-CHCHCHCH                                           681                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Cl,4-Me                                              682                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Cl,6-Me                                              683                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Me,4-Cl                                              684                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Cl,4-Cl,6-Cl                                         685                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Me,4-Me,5-Me                                         686                                                                               t-Bu                                                                              Cl O H  O Me CO   2-Me,4-Me,6-Me                                         687                                                                               t-Bu                                                                              Br O H  O Me CO   H                                                      688                                                                               t-Bu                                                                              OMe                                                                               O H  O Me CO   H                                                      689                                                                               t-Bu                                                                              SMe                                                                               O H  O Me CO   H                                                      690                                                                               t-Bu                                                                              Cl O H  O i-Pr                                                                              CO   H                                                      694                                                                               t-Bu                                                                              Cl O H  O Cl CH.sub.2                                                                            H                                                      695                                                                               t-Bu                                                                              Cl O H  O Cl CH.sub.2                                                                            4-Cl                                                   696                                                                               t-Bu                                                                              Cl O H  O Cl CH.sub.2                                                                            4-Me                                                   697                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            H                                                      698                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Cl                                                   699                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            3-Cl                                                   700                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-Cl                                                   701                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-F                                                    702                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-F                                                    703                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Br                                                   704                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-Br                                                   705                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-I                                                    706                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Me                                                   707                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            3-Me                                                   708                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-Me                                                   709                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-Et                                                   710                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-Bu                                                   711                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-i-Pr                                                 712                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-t-Bu                                                 713                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-CF.sub.3                                             714                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-NO.sub.2                                             715                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-CN                                                   716                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-OMe                                                  717                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-OEt                                                  718                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-SMe                                                  719                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            4-NMe.sub.2                                            720                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-F,4-F                                                721                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-F,6-F                                                722                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Cl,4-Cl                                              723                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Cl,6-Cl                                              724                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            3-Cl,4-Cl                                              725                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            3-Cl,5-Cl                                              726                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Cl,4-NO.sub.2                                        727                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-NO.sub.2,4-Cl                                        728                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Me,4-Me                                              729                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Me,6-Me                                              730                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            3-Me,4-Me                                              731                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            3-Me,5-Me                                              732                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            3,4-CHCHCHCH                                           733                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Cl,4-Me                                              734                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Cl,6-Me                                              735                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Me,4-Cl                                              736                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Cl,4-Cl,6-Cl                                         737                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Me,4-Me,5-Me                                         738                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2                                                                            2-Me,4-Me,6-Me                                         739                                                                               t-Bu                                                                              Br O H  O Me CH.sub.2                                                                            H                                                      740                                                                               t-Bu                                                                              OMe                                                                               O H  O Me CH.sub.2                                                                            H                                                      741                                                                               t-Bu                                                                              SMe                                                                               O H  O Me CH.sub.2                                                                            H                                                      742                                                                               t-Bu                                                                              Cl O H  O i-Pr                                                                              CH.sub.2                                                                            H                                                      743                                                                               t-Bu                                                                              Cl O H  O Me CHMe H                                                      744                                                                               t-Bu                                                                              Cl O H  O Me CHMe 4-Cl                                                   745                                                                               t-Bu                                                                              Cl O H  O Me CHMe 4-Me                                                   746                                                                               t-Bu                                                                              Cl O H  O Me CHMe 4-OMe                                                  747                                                                               t-Bu                                                                              Cl O H  O i-Pr                                                                              CHMe H                                                      748                                                                               t-Bu                                                                              Cl O H  O i-Pr                                                                              CHMe 4-Cl                                                   749                                                                               t-Bu                                                                              Cl O H  O i-Pr                                                                              CHMe 4-Me                                                   750                                                                               t-Bu                                                                              Cl O H  O i-Pr                                                                              CHMe 4-OMe                                                  763                                                                               t-Bu                                                                              Cl O H  O Cl COCH.sub.2                                                                          H                                                      767                                                                               t-Bu                                                                              Cl O H  O Br COCH.sub.2                                                                          H                                                      769                                                                               t-Bu                                                                              Cl O H  O Me COCH.sub.2                                                                          H                                                      777                                                                               t-Bu                                                                              Cl O H  O Me CH.sub.2 CH.sub.2                                                                   H                                                      781                                                                               t-Bu                                                                              Cl S H  O H  CHOH H                                                      782                                                                               t-Bu                                                                              Cl S H  O H  CHOH 4-Cl                                                   783                                                                               t-Bu                                                                              Cl S H  O Cl CHOH H                                                      784                                                                               t-Bu                                                                              Cl S H  O Cl CHOH 4-Cl                                                   785                                                                               t-Bu                                                                              Cl S H  O Me CHOH H                                                      786                                                                               t-Bu                                                                              Cl S H  O Me CHOH 4-Cl                                                   787                                                                               t-Bu                                                                              Cl S H  O Me CHOH 4-F                                                    788                                                                               t-Bu                                                                              Cl S H  O Me CHOH 4-Me                                                   789                                                                               t-Bu                                                                              Cl S H  O Me CHOH 2-Cl,4-Cl                                              790                                                                               t-Bu                                                                              Cl S H  O Me CHOH 2-Me,4-Me                                              791                                                                               t-Bu                                                                              Cl S H  O H  CHOMe                                                                               H                                                      792                                                                               t-Bu                                                                              Cl S H  O H  CHOMe                                                                               4-Cl                                                   793                                                                               t-Bu                                                                              Cl S H  O Me CHOMe                                                                               H                                                      794                                                                               t-Bu                                                                              Cl S H  O Me CHOMe                                                                               4-Cl                                                   795                                                                               t-Bu                                                                              Cl S H  O Me CHOMe                                                                               4-F                                                    796                                                                               t-Bu                                                                              Cl S H  O Me CHOMe                                                                               4-Me                                                   797                                                                               t-Bu                                                                              Cl S H  O Me CHOMe                                                                               2-Cl,4-Cl                                              798                                                                               t-Bu                                                                              Cl S H  O Me CHOMe                                                                               2-Me,4-Me                                              799                                                                               t-Bu                                                                              Cl S H  O Me CHOEt                                                                               H                                                      800                                                                               t-Bu                                                                              Cl S H  O Me CHOPr                                                                               H                                                      801                                                                               t-Bu                                                                              Cl S H  O H  C(OMe).sub.2                                                                        H                                                      802                                                                               t-Bu                                                                              Cl S H  O H  C(OMe).sub.2                                                                        4-Cl                                                   803                                                                               t-Bu                                                                              Cl S H  O Cl C(OMe).sub.2                                                                        H                                                      804                                                                               t-Bu                                                                              Cl S H  O Cl C(OMe).sub.2                                                                        4-Cl                                                   805                                                                               t-Bu                                                                              Cl S H  O Me C(OMe).sub.2                                                                        H                                                      806                                                                               t-Bu                                                                              Cl S H  O Me C(OMe).sub.2                                                                        4-Cl                                                   807                                                                               t-Bu                                                                              Cl S H  O Me C(OMe).sub.2                                                                        4-F                                                    808                                                                               t-Bu                                                                              Cl S H  O Me C(OMe).sub.2                                                                        4-Me                                                   809                                                                               t-Bu                                                                              Cl S H  O Me C(OMe).sub.2                                                                        2-Cl,4-Cl                                              810                                                                               t-Bu                                                                              Cl S H  O Me C(OMe).sub.2                                                                        2-Me,4-Me                                              811                                                                               t-Bu                                                                              Cl S H  O H  CHCl H                                                      812                                                                               t-Bu                                                                              Cl S H  O H  CHCl 4-Cl                                                   813                                                                               t-Bu                                                                              Cl S H  O Cl CHCl H                                                      814                                                                               t-Bu                                                                              Cl S H  O Cl CHCl 4-Cl                                                   815                                                                               t-Bu                                                                              Cl S H  O Me CHCl H                                                      816                                                                               t-Bu                                                                              Cl S H  O Me CHCl 4-Cl                                                   817                                                                               t-Bu                                                                              Cl S H  O Me CHCl 4-F                                                    818                                                                               t-Bu                                                                              Cl S H  O Me CHCl 4-Me                                                   819                                                                               t-Bu                                                                              Cl S H  O Me CHCl 2-Cl,4-Cl                                              820                                                                               t-Bu                                                                              Cl S H  O Me CHCl 2-Me,4-Me                                              __________________________________________________________________________

                  TABLE 3                                                          ______________________________________                                          ##STR9##                                                                      No.  R      A      X   R.sup.1                                                                             Y    Z.sup.5                                                                             Z.sup.6                                  ______________________________________                                         841  t-Bu   Cl     S   H    O    Me   CH.sub.2 OH                              842  t-Bu   Cl     S   H    O    Me   CH(OH)CH.sub.3                           843  t-Bu   Cl     S   H    O    Me   CH(OH)CH.sub.2 CH.sub.3                  844  t-Bu   Cl     S   H    O    Me   CH(OH)CH.sub.2 CH.sub.2 CH.sub.3         845  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 CH.sub.2 OH            846  t-Bu   Cl     S   H    O    Me   CH.sub.2 OCOCH.sub.3                     847  t-Bu   Cl     S   H    O    Me   CH.sub.2 OCOEt                           848  t-Bu   Cl     S   H    O    Me   CHMeOCOCH.sub.3                          849  t-Bu   Cl     S   H    O    Me   CHEtOCOCH.sub.3                          850  t-Bu   Cl     S   H    O    Me   CH.sub.2 OMe                             851  t-Bu   Cl     S   H    O    Me   CH.sub.2 OEt                             852  t-Bu   Cl     S   H    O    Me   CH.sub.2 OPr                             853  t-Bu   Cl     S   H    O    Me   CH.sub.2 Oi-Pr                           854  t-Bu   Cl     S   H    O    Me   CHMeOMe                                  855  t-Bu   Cl     S   H    O    Me   CHMeOET                                  856  t-Bu   Cl     S   H    O    Me   CHMeOPr                                  857  t-Bu   Cl     S   H    O    Me   CHEtOMe                                  858  t-Bu   Cl     S   H    O    Me   CHEtOEt                                  859  t-Bu   Cl     S   H    O    Me   C(OMe).sub.2 CH.sub.3                    860  t-Bu   Cl     S   H    O    Me   C(OEt).sub.2 CH.sub.3                    861  t-Bu   Cl     S   H    O    Me   C(OMe).sub.2 CH.sub.2 CH.sub.3           862  t-Bu   Cl     S   H    O    Me   C(OEt).sub.2 CH.sub.2 CH.sub.3           863  t-Bu   Cl     S   H    O    Me   CH.sub.2 SMe                             864  t-Bu   Cl     S   H    O    Me   CH.sub.2 SEt                             865  t-Bu   Cl     S   H    O    Me   CH.sub.2 SPr                             866  t-Bu   Cl     S   H    O    Me   CH.sub.2 S-i-Pr                          867  t-Bu   Cl     S   H    O    Me   CH.sub.2 SOMe                            868  t-Bu   Cl     S   H    O    Me   CH.sub.2 SOEt                            869  t-Bu   Cl     S   H    O    Me   CH.sub.2 SOPr                            870  t-Bu   Cl     S   H    O    Me   CH.sub.2 SOi-Pr                          871  t-Bu   Cl     S   H    O    Me   CH.sub.2 SO.sub.2 Me                     872  t-Bu   Cl     S   H    O    Me   CH.sub.2 SO.sub.2 Et                     873  t-Bu   Cl     S   H    O    Me   CH.sub.2 SO.sub.2 Pr                     874  t-Bu   Cl     S   H    O    Me   CH.sub.2 SO.sub.2i-Pr                    875  t-Bu   Cl     S   H    O    Me   CH.sub.2 NMe.sub.2                       876  t-Bu   Cl     S   H    O    Me   CH.sub.2 NEt.sub.2                       877  t-Bu   Cl     S   H    O    Me   CH.sub.2 NPr.sub.2                       878  t-Bu   Cl     S   H    O    Me   CH.sub.2 COCH.sub.3                      879  t-Bu   Cl     S   H    O    Me   CH.sub.2 COEt                            880  t-Bu   Cl     S   H    O    Me   CH.sub.2 COPr                            881  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 COCH.sub.3             882  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 COEt                   883  t-Bu   Cl     S   H    O    Me   CH.sub.2 CO.sub.2 Me                     884  t-Bu   Cl     S   H    O    Me   CH.sub.2 CO.sub.2 Et                     885  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 CO.sub.2 Me            886  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 CO.sub.2 Et            887  t-Bu   Cl     S   H    O    Me   CH.sub.2 CN                              888  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 CN                     889  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 CH.sub.2 CN            890  t-Bu   Cl     S   H    O    Me   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            CN                                       891  t-Bu   Cl     S   H    O    Me   CHCNCH.sub.3                             892  t-Bu   Cl     S   H    O    Me   CHCNCH.sub.2 CH.sub.3                    893  t-Bu   Cl     S   H    O    Me   CHCNCH.sub.2 CH.sub.2 CH.sub.3           894  t-Bu   Cl     S   H    O    Me   CHNOMe                                   895  t-Bu   Cl     S   H    O    Me   CMeNOMe                                  896  t-Bu   Cl     S   H    O    Me   CMeNOEt                                  897  t-Bu   Cl     S   H    O    Me   CEtNOMe                                  898  t-Bu   Cl     S   H    O    Me   CEtNOEt                                  899  t-Bu   Cl     S   H    O    Cl   CH.sub.2 OMe                             900  t-Bu   Cl     S   H    O    Cl   CH.sub.2 OEt                             901  t-Bu   Cl     S   H    O    Me   OCH.sub.2 OMe                            902  t-Bu   Cl     S   H    O    Me   OCH.sub.2 OEt                            903  t-Bu   Cl     S   H    O    Me   OCH.sub.2 OPr                            904  t-Bu   Cl     S   H    O    Me   OCH.sub.2 Oi-Pr                          905  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 OMe                   906  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 OEt                   907  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 OPr                   908  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 Oi-Pr                 909  t-Bu   Cl     S   H    O    Me   OCH.sub.2 SMe                            910  t-Bu   Cl     S   H    O    Me   OCH.sub.2 SEt                            911  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 SMe                   912  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 SEt                   913  t-Bu   Cl     S   H    O    Me   OCH.sub.2 SOMe                           914  t-Bu   Cl     S   H    O    Me   OCH.sub.2 SO.sub.2 Me                    915  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 SOMe                  916  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 SO.sub.2 Me           917  t-Bu   Cl     S   H    O    Me   OCH.sub.2 NMe.sub.2                      918  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 NMe.sub.2             919  t-Bu   Cl     S   H    O    Me   OCH.sub.2 COCH.sub.3                     920  t-Bu   Cl     S   H    O    Me   OCH.sub.2 COEt                           921  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 COCH.sub.3            922  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 COEt                  923  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CO.sub.2 Me                    924  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CO.sub.2 Et                    925  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 CO.sub.2 Me           926  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 CO.sub.2 Et           927  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CN                             928  t-Bu   Cl     S   H    O    Me   OCH.sub.2 CH.sub.2 CN                    929  t-Bu   Cl     S   H    O    H    OCH.sub.2 OMe                            930  t-Bu   Cl     S   H    O    H    OCH.sub.2 OEt                            931  t-Bu   Cl     S   H    O    Me   COCH.sub.2 F                             932  t-Bu   Cl     S   H    O    Me   COCH.sub.2 Cl                            933  t-Bu   Cl     S   H    O    Me   COCH.sub.2 Br                            934  t-Bu   Cl     S   H    O    Me   COCF.sub.3                               935  t-Bu   Cl     S   H    O    Me   COCHClCH.sub.3                           936  t-Bu   Cl     S   H    O    Me   COCHBrCH.sub.3                           937  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CF.sub.3                      938  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 F                    939  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 Cl                   940  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 Br                   941  t-Bu   Cl     S   H    O    Me   COCH.sub.2 OMe                           942  t-Bu   Cl     S   H    O    Me   COCH.sub.2 OEt                           943  t-Bu   Cl     S   H    O    Me   COCH.sub.2 OPr                           944  t-Bu   Cl     S   H    O    Me   COCHMeOMe                                945  t-Bu   Cl     S   H    O    Me   COCHMeOEt                                946  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 OMe                  947  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 OEt                  948  t-Bu   Cl     S   H    O    Me   COCH.sub.2 SMe                           949  t-Bu   Cl     S   H    O    Me   COCH.sub.2 SEt                           950  t-Bu   Cl     S   H    O    Me   COCH.sub.2 SPr                           951  t-Bu   Cl     S   H    O    Me   COCHMeSMe                                952  t-Bu   Cl     S   H    O    Me   COCHMeSEt                                953  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 SMe                  954  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 SEt                  955  t-Bu   Cl     S   H    O    Me   COCH.sub.2 SOMe                          956  t-Bu   Cl     S   H    O    Me   COCH.sub.2 SOEt                          957  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 SOMe                 958  t-Bu   Cl     S   H    O    Me   COCH.sub.2 SO.sub.2 Me                   959  t-Bu   Cl     S   H    O    Me   COCH.sub.2 SO.sub.2 Et                   960  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 SO.sub.2 Me          961  t-Bu   Cl     S   H    O    Me   COCH.sub.2 NMe.sub.2                     962  t-Bu   Cl     S   H    O    Me   COCH.sub.2 NEt.sub.2                     963  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 NMe.sub.2            964  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 NEt.sub.2            965  t-Bu   Cl     S   H    O    Me   COCH.sub.2 COCH.sub.3                    966  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CO.sub.2 Me                   967  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CO.sub.2 Et                   968  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 CO.sub.2 Me          969  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 CO.sub.2 Et          970  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CN                            971  t-Bu   Cl     S   H    O    Me   COCH.sub.2 CH.sub.2 CN                   972  t-Bu   Cl     S   H    O    Me   COCHMeCN                                 973  t-Bu   Cl     S   H    O    H    COCH.sub.2 Cl                            974  t-Bu   Cl     S   H    O    H    COCH.sub.2 Br                            975  t-Bu   Cl     S   H    O    H    COCH.sub.2 F                             976  t-Bu   Cl     S   H    O    H    COCH.sub.2 CH.sub.2 Cl                   977  t-Bu   Cl     S   H    O    H    COCH.sub.2 CH.sub.2 F                    978  t-Bu   Cl     S   H    O    H    COCH.sub.2 OMe                           979  t-Bu   Cl     S   H    O    H    COCH.sub.2 OEt                           980  t-Bu   Cl     S   H    O    H    COCH.sub.2 OPr                           981  t-Bu   Cl     S   H    O    H    COCH.sub.2 SMe                           982  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 Cl                            983  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 Br                            984  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 F                             985  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 CH.sub.2 Cl                   986  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 CH.sub.2 F                    987  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 OMe                           988  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 OEt                           989  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 OPr                           990  t-Bu   Cl     S   H    O    Cl   COCH.sub.2 SMe                           991  t-Bu   Cl     O   H    O    Me   CH.sub.2 OH                              992  t-Bu   Cl     O   H    O    Me   CH(OH)CH.sub.3                           993  t-Bu   Cl     O   H    O    Me   CH(OH)CH.sub.2 CH.sub.3                  994  t-Bu   Cl     O   H    O    Me   CH(OH)CH.sub.2 CH.sub.2 CH.sub.3         995  t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub.2 CH.sub.2 OH            996  t-Bu   Cl     O   H    O    Me   CH.sub.2 OCOCH.sub.3                     997  t-Bu   Cl     O   H    O    Me   CH.sub.2 OCOEt                           998  t-Bu   Cl     O   H    O    Me   CHMeOCOCH.sub.3                          999  t-Bu   Cl     O   H    O    Me   CHEtOCOCH.sub.3                          1000 t-Bu   Cl     O   H    O    Me   CH.sub.2 OMe                             1001 t-Bu   Cl     O   H    O    Me   CH.sub.2 OEt                             1002 t-Bu   Cl     O   H    O    Me   CH.sub.2 OPr                             1003 t-Bu   Cl     O   H    O    Me   CH.sub.2 Oi-Pr                           1004 t-Bu   Cl     O   H    O    Me   CHMeOMe                                  1005 t-Bu   Cl     O   H    O    Me   CHMeOEt                                  1006 t-Bu   Cl     O   H    O    Me   CHMeOPr                                  1007 t-Bu   Cl     O   H    O    Me   CHEtOMe                                  1008 t-Bu   Cl     O   H    O    Me   CHEtOEt                                  1009 t-Bu   Cl     O   H    O    Me   C(OMe).sub.2 CH.sub.3                    1010 t-Bu   Cl     O   H    O    Me   C(OEt).sub.2 CH.sub.3                    1011 t-Bu   Cl     O   H    O    Me   C(OMe).sub.2 CH.sub.2 CH.sub.3           1012 t-Bu   Cl     O   H    O    Me   C(OEt).sub.2 CH.sub.2 CH.sub.3           1013 t-Bu   Cl     O   H    O    Me   CH.sub.2 SMe                             1014 t-Bu   Cl     O   H    O    Me   CH.sub.2 SEt                             1015 t-Bu   Cl     O   H    O    Me   CH.sub.2 SPr                             1016 t-Bu   Cl     O   H    O    Me   CH.sub.2 S-i-Pr                          1017 t-Bu   Cl     O   H    O    Me   CH.sub.2 SOMe                            1018 t-Bu   Cl     O   H    O    Me   CH.sub.2 SOEt                            1019 t-Bu   Cl     O   H    O    Me   CH.sub.2 SOPr                            1020 t-Bu   Cl     O   H    O    Me   CH.sub.2 SOi-Pr                          1021 t-Bu   Cl     O   H    O    Me   CH.sub.2 SO.sub.2 Me                     1022 t-Bu   Cl     O   H    O    Me   CH.sub.2 SO.sub.2 Et                     1023 t-Bu   Cl     O   H    O    Me   CH.sub.2 SO.sub.2 Pr                     1024 t-Bu   Cl     O   H    O    Me   CH.sub.2 SO.sub.2i-Pr                    1025 t-Bu   Cl     O   H    O    Me   CH.sub.2 NMe.sub.2                       1026 t-Bu   Cl     O   H    O    Me   CH.sub.2 NEt.sub.2                       1027 t-Bu   Cl     O   H    O    Me   CH.sub.2 NPr.sub.2                       1028 t-Bu   Cl     O   H    O    Me   CH.sub.2 COCH.sub.3                      1029 t-Bu   Cl     O   H    O    Me   CH.sub.2 COEt                            1030 t-Bu   Cl     O   H    O    Me   CH.sub.2 COPr                            1031 t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub.2 COCH.sub.3             1032 t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub.2 COEt                   1033 t-Bu   Cl     O   H    O    Me   CH.sub.2 CO.sub.2 Me                     1034 t-Bu   Cl     O   H    O    Me   CH.sub.2 SO.sub.2 Et                     1035 t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub. 2 CO.sub.2 Me           1036 t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub.2 CO.sub.2 Et            1037 t-Bu   Cl     O   H    O    Me   CH.sub.2 CN                              1038 t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub.2 CN                     1039 t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub.2 CH.sub.2 CN            1040 t-Bu   Cl     O   H    O    Me   CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2                                            CN                                       1041 t-Bu   Cl     O   H    O    Me   CHCNCH.sub.3                             1042 t-Bu   Cl     O   H    O    Me   CHCNCH.sub.2 CH.sub.3                    1043 t-Bu   Cl     O   H    O    Me   CHCNCH.sub.2 CH.sub.2 CH.sub.3           1044 t-Bu   Cl     O   H    O    Me   CHNOMe                                   1045 t-Bu   Cl     O   H    O    Me   CMeNOMe                                  1046 t-Bu   Cl     O   H    O    Me   CMeNOEt                                  1047 t-Bu   Cl     O   H    O    Me   CEtNOMe                                  1048 t-Bu   Cl     O   H    O    Me   CEtNOEt                                  1049 t-Bu   Cl     O   H    O    Cl   CH.sub.2 OMe                             1050 t-Bu   Cl     O   H    O    Cl   CH.sub.2 OEt                             1051 t-Bu   Cl     O   H    O    Me   OCH.sub.2 OMe                            1052 t-Bu   Cl     O   H    O    Me   OCH.sub.2 OEt                            1053 t-Bu   Cl     O   H    O    Me   OCH.sub.2 OPr                            1054 t-Bu   Cl     O   H    O    Me   OCH.sub.2 Oi-Pr                          1055 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 OMe                   1056 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 OEt                   1057 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 OPr                   1058 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 Oi-Pr                 1059 t-Bu   Cl     O   H    O    Me   OCH.sub.2 SMe                            1060 t-Bu   Cl     O   H    O    Me   OCH.sub.2 SEt                            1061 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 SMe                   1062 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 SEt                   1063 t-Bu   Cl     O   H    O    Me   OCH.sub.2 SOMe                           1064 t-Bu   Cl     O   H    O    Me   OCH.sub.2 SO.sub.2 Me                    1065 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 SOMe                  1066 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 SO.sub.2 Me           1067 t-Bu   Cl     O   H    O    Me   OCH.sub.2 NMe.sub.2                      1068 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 NMe.sub.2             1069 t-Bu   Cl     O   H    O    Me   OCH.sub.2 COCH.sub.3                     1070 t-Bu   Cl     O   H    O    Me   OCH.sub.2 COEt                           1071 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 COCH.sub.3            1072 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 COEt                  1073 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CO.sub.2 Me                    1074 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CO.sub.2 Et                    1075 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 CO.sub.2 Me           1076 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 CO.sub.2 Et           1077 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CN                             1078 t-Bu   Cl     O   H    O    Me   OCH.sub.2 CH.sub.2 CN                    1081 t-Bu   Cl     O   H    O    Me   COCH.sub.2 F                             1082 t-Bu   Cl     O   H    O    Me   COCH.sub.2 Cl                            1083 t-Bu   Cl     O   H    O    Me   COCH.sub.2 Br                            1084 t-Bu   Cl     O   H    O    Me   COCF.sub.3                               1085 t-Bu   Cl     O   H    O    Me   COCHClCH.sub.3                           1086 t-Bu   Cl     O   H    O    Me   COCHBrCH.sub.3                           1087 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CF.sub.3                      1088 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 F                    1089 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 Cl                   1090 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 Br                   1091 t-Bu   Cl     O   H    O    Me   COCH.sub.2 OMe                           1092 t-Bu   Cl     O   H    O    Me   COCH.sub.2 OEt                           1093 t-Bu   Cl     O   H    O    Me   COCH.sub.2 OPr                           1094 t-Bu   Cl     O   H    O    Me   COCHMeOMe                                1095 t-Bu   Cl     O   H    O    Me   COCHMeOEt                                1096 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 OMe                  1097 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 OEt                  1098 t-Bu   Cl     O   H    O    Me   COCH.sub.2 SMe                           1099 t-Bu   Cl     O   H    O    Me   COCH.sub.2 SEt                           1100 t-Bu   Cl     O   H    O    Me   COCH.sub.2 SPr                           1101 t-Bu   Cl     O   H    O    Me   COCHMeSMe                                1102 t-Bu   Cl     O   H    O    Me   COCHMeSEt                                1103 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 SMe                  1104 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 SEt                  1105 t-Bu   Cl     O   H    O    Me   COCH.sub.2 SOMe                          1106 t-Bu   Cl     O   H    O    Me   COCH.sub.2 SOEt                          1107 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 SOMe                 1108 t-Bu   Cl     O   H    O    Me   COCH.sub.2 SO.sub.2 Me                   1109 t-Bu   Cl     O   H    O    Me   COCH.sub.2 SO.sub.2 Et                   1110 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 SO.sub.2 Me          1111 t-Bu   Cl     O   H    O    Me   COCH.sub.2 NMe.sub.2                     1112 t-Bu   Cl     O   H    O    Me   COCH.sub.2 NEt.sub.2                     1113 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 NMe.sub.2            1114 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 NEt.sub.2            1115 t-Bu   Cl     O   H    O    Me   COCH.sub.2 COCH.sub.3                    1116 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CO.sub.2 Me                   1117 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CO.sub.2 Et                   1118 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 CO.sub.2 Me          1119 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 CO.sub.2 Et          1120 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CN                            1121 t-Bu   Cl     O   H    O    Me   COCH.sub.2 CH.sub.2 CN                   1122 t-Bu   Cl     O   H    O    Me   COCHMeCN                                 1132 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 Cl                            1133 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 Br                            1134 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 F                             1135 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 CH.sub.2 Cl                   1136 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 CH.sub.2 F                    1137 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 OMe                           1138 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 OEt                           1139 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 OPr                           1140 t-Bu   Cl     O   H    O    Cl   COCH.sub.2 SMe                           1141 t-Bu   Cl     S   H    O    Me   NHSO.sub.2 Me                            1142 t-Bu   Cl     S   H    O    Me   NHCONMe.sub.2                            1143 t-Bu   Cl     S   H    O    Me   C(Me)NNMe.sub.2                          ______________________________________                                    

Preferred compounds according to the present invention include:

2-t-butyl-4-chloro-5-[2-2,6-dimethyl-4-(4-methylphenoxy)phenoxy ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR10##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-phenoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR11##

2-t-butyl-4-chloro-5-[2-{2,6-dimethyl-4-(2,4-difluorobenzoyl)phenoxy}ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR12##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-ethoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR13##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-methoxy-methylphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR14##

The compound numbers in Tables 1 to 3 are referred to in preparation examples, formulation examples and test examples, which will be mentioned below.

The compounds of the present invention can be prepared by reacting a compound of the general formula (II): ##STR15## with a compound of the general formula (III): ##STR16## wherein R, A, R¹, Y, and Z¹ -Z⁴ have the same meanings as defined above, and X' and X" represent halogen atom, --SM or --OM in which M means hydrogen atom or alkali metal atom.

In general, it is preferable to use --SM or --OM as X" in the general formula (III) when X' in the general formula (II) is halogen atom, and to use halogen atom as X" in the general formula (III) when X' in the general formula (II) is --SM or --OM (wherein M represents hydrogen atom or alkali metal atom), with the proviso that when X' is halogen atom, X" represents --Sm or --OM, and when X' is --SM or --OM, X" represents halogen atom.

It is also preferable to prepare the compounds of the present invention in the presence of appropriate bases and in solvents which do not affect the reaction. When M is alkali metal atom, the presence of the base is not necessarily needed.

As the solvents in the present invention can be used lower alcohols such as methanol, ethanol, etc.; ketones such as acetone, methylethylketone, etc.; hydrocarbons such as benzene, toluene, etc.; ethers such as isopropylether, tetrahydrofuran, 1,4-dioxane, etc.; amides such as N,N-dimethylformamide, hexamethyl phosphoric triamides, etc.; halogenated hydrocarbons such as dichloromethane, dichloroethane, etc. As necessary, mixtures of these solvens or mixtures of these solvents and water can also be used.

Inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen-carbonate, etc., and organic bases such as sodium methoxide, sodium ethoxide, triethylamine, pyridine, etc. can be used as the base. If necessary, tetraammonium salts, for example, triethylbenzylammonium chloride, etc., may be added to the reaction system as catalyst.

The reaction temperature may be in a range of from -20° C. to the boiling point of the solvent to be used in the reaction. The reaction temperature is preferably in a range of from -5° C. to the boiling point of the solvent to be used in the reaction.

The ratio of the raw material can be optionally selected, but it is advantageous to conduct the reaction using equimolar or nearly equimolar amount of the materials.

Preparation of compounds of the present invention is described in more detail by the way of the following examples which are not to restrict to the invention.

PREPARATION EXAMPLE 1 Preparation of 2-t-butyl-4-chloro-5-(2'-[2",6"-dimethylphenoxy) ethylthio]-3-(2H)-pyridazinone (Compound No. 24)

In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 2.3 g of 2-(2',6'-dimethylphenoxy)ethyl bromide, and thereto were added 1.1 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give crystals. The crystals thus obtained were washed with n-hexane to give 3.5 g of the intended compound. m.p. 104.3°˜105.2° C.

PREPARATION EXAMPLE 2 Preparation of 2-t-butyl-4-chloro-5-(2'-[2",6"-dimethyl-4"-butylcarbonylphenoxy)ethylthio]-3-(2H)-pyridazinone (Compound No. 78)

In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 3.0 g of 2-(2',6'-dimethyl-4'butylcarbonylphenoxyethyl bromide and thereto were added 1.5 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give a crude product. The crude product thus obtained was purified by means of column chromatography (on silica gel, eluting with benzene) to give 3.3 g of the intended compound as an oil.

PREPARATION EXAMPLE 3 Preparation of 2-t-butyl-4-chloro-5-[2'-(2",6"-dimethyl-4"-benzoylphenoxy)ethylthio]-3-(2H)-pyridazinone (Compound No. 465)

In 50 ml of N,N-dimethylformamide were dissolved 6.6 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 10 g of 2-(2',6'-dimethyl-4'-benzoylphenoxy)ethyl bromide, and thereto was added 5 g of anhydrous sodium carbonate. The solution was stirred at room temperature for seventeen hours. The resulting solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give a crude product. The crude product thus obtained was purified by means of column chromatography (on silica gel, eluting with benzene) and crystallization (from 50 ml of n-hexanediethyl ether (4:1)) to give 13.3 g of the intended compound. m.p. 94.6°˜96.2° C.

PREPARATION EXAMPLE 4 Preparation of 2-t-butyl-4-chloro-5-[2{-2,6-dimethyl-4-(4-methylphenoxy)phenoxy}ethylthio]-3(2H)-pyridazinone (Compound No. 429).

In 10 ml of N,N-dimethylformamide were dissolved 1.5 g of 2-t-butyl-4-chloro-5-mercapt-3(2H)-pyridazinone and 2.3 g of 2-{2,6-dimethyl-4-(4-methylphenoxy)phenoxy}ethylbromide, and thereto was added 1.0 g of anhydrous sodium carbonate. The mixture was stirred for 15 hours at room temperature. The resulting solution was poured into water (50 ml) and then extracted with 50 ml of diethyl ether and further with 50 ml of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give 3.2 g of a crude product. The crude product was recrystallized from benzenehexane (1:3)(20 ml) to obtain 2.5 g of the intended compound. m.p.: 137.7°-140.7° C.

The physical properties of the compounds prepared according to one of the methods of the Preparation Examples 1 to 4 are shown in the following Table 4.

                  TABLE 4                                                          ______________________________________                                         No.     m.p. (°C.)                                                                            No.      m.p. (°C.)                               ______________________________________                                         12      109.2-111.6   56       86.4-91.5                                       13      oil           61       109.7-112.0                                     14      oil           70       oil                                             15      oil           71       152.9-153.7                                     16      61.0-63.0     72       116.9-118.2                                     17      65.0-70.0     73       106.9-108.6                                     18      oil           74       127.9-130.1                                     19      oil           75       126.1-129.2                                     21      87.0-88.5     76       oil                                             22      96.8-98.5     77       152.7-156.4                                     23      112.4-113.3   78       oil                                             24      104.3-105.2   79       oil                                             25      oil           80       oil                                             26      78.3-80.7     82       107.0-108.8                                     27       98.6-102.1   84       79.7-80.8                                       28      oil           85       90.0-91.5                                       29      oil           87       oil                                             30      oil           88       103.5-104.8                                     31      95.7-98.0     89       119.8-124.5                                     32      109.0-111.2   90       oil                                             33      106.6-109.2   92       117.2-120.1                                     34      95.4-97.0     93       oil                                             36      oil           94       108.2-109.2                                     38      123.4-127.3   95       oil                                             40      94.0-96.0     97       oil                                             41      oil           98       oil                                             44      oil           99       oil                                             45      oil           112      107.7-108.3                                     46      115.0-118.1   113      86.2-88.5                                       49      oil           148      oil                                             53      oil           150      oil                                             55      92.8-93.6     151      88.0-89.0                                                             161      55.0-60.0                                                             270      156.0-160.5                                     174     oil           271      116.1-117.6                                     202     85.0-87.0     272      159.9-161.3                                     219     126.5-127.7   273      122.0-124.8                                     223     111.1-113.5   275       98.1-104.2                                     224      97.0-101.0   277      143.1-145.6                                     225     oil           279      107.6-109.5                                     226     124.6-129.5   280      102.8-106.5                                     227     135.6-139.2   283      86.7-88.1                                       228     131.1-132.6   284      108.8-110.5                                     229     133.2-134.7   285       94.5-100.0                                     230     120.0-124.0   287      173.3-176.3                                     232     79.0-80.3     288      86.6-87.9                                       233     142.5-146.5   289      147.1-148.3                                     235     85.0-87.0     290      73.1-75.5                                       236     96.0-98.0     292      oil                                             239     155.7-157.4   293      64.1-64.2                                       240     oil           294      103.4-104.4                                     241     108.2-111.8   343      96.1-97.3                                       248     149.5-151.2   344      117.9-120.9                                     250     137.9-139.2   360      oil                                             251     88.0-93.0     421      120.3-128.2                                     256     130.6-134.1   463      150.2-151.8                                     265     112.9-114.5   465      94.6-96.2                                       266     171.0-173.8   466      156.9-158.1                                     267     150.6-152.9   467      oil                                             268     131.5-133.5   468      142.2-144.1                                     269     135.2-137.8   470      oil                                             472     153.1-154.5   656      113.0-116.0                                     474     129.2-131.4   660      143.9-145.6                                     475     oil           662      193.0-196.0                                     476     oil           664      168.6-170.9                                     480     138.0-140.0   670      153.0-154.3                                     482     162.0-164.6   672      143.0-144.8                                     484     125.1-126.4   673      177.5-179.0                                     490     108.9-111.2   676      122.7-123.4                                     492     126.5- 128.0  678      157.6-159.1                                     493     158.7-161.3   680      137.1-138.1                                     494     134.4-135.4   694      139.2-140.4                                     496     121.7-122.5   697      163.4-165.0                                     498     113.8-115.9   698      179.8-182.2                                     500     135.3-137.3   699      116.7-117.7                                     514     oil           722      58.0-62.0                                       517     123.1-126.1   725      130.0-131.0                                     518     136.4-137.5   111      91.1-92.1                                       519     98.3-99.2     491      212.6-213.6                                     520     oil           477      116.6-118.6                                     527     105.9-107.6   306      125.9-127.6                                     542     115.2-116.4   671      224.5-226.5                                     545     130.7-132.5   657      137.6-139.1                                     643     156.8-158.0   152       98.9-101.5                                     646     202.3-204.0   489      161.0-163.6                                     647     135.8-137.8   83       121.0-122.0                                     652     163.9-166.0   278      142.7-144.7                                     654     168.9-170.1   153      87.5-90.0                                       655     134.1-135.9                                                            198     93.3-94.8     609      153.1-157.0                                     100     104.7-106.7   610      134.0-136.0                                     102     135.4-136.5   612      180.0-183.0                                     127     119.0-120.6   618      126.9-128.9                                     128     93.2-95.2     661      165.0-167.0                                     129     74.8-76.5     668      145.8-146.7                                     131     118.5-121.3   702      57.0-60.0                                       134     141.9-142.7   704       98.8-101.1                                     135     125.3-127.4   708      143.7-145.3                                     199     70.4-71.2     720      118.5-120.1                                     296     166.8-167.8   843      147.8-150.4                                     323     105.0-107.2   850      67.0-70.0                                       324     81.1-83.6     851      oil                                             426     119.3-120.4   852      oil                                             427     102.2-102.9   857      oil                                             429     137.7-140.7   863      oil                                             430     95.3-98.0     895      106.7-109.2                                     432     112.8-113.4   1000     105.0-107.0                                     438     102.2-102.9   1001     103.7-105.7                                     443     120.0-123.2   1002     94.3-96.7                                       481     142.4-143.5   1045     141.5-143.1                                     488     123.8-124.9   1141     216.0-218.0                                     522     oil           1142     173.6-175.8                                     524     oil           1143     121.4-124.1                                     528     103.4-104.5   589      oil                                             540     93.0-94.1     597      oil                                             606     167.5-170.3   777      101.5-105.6                                     ______________________________________                                    

When the compounds according to the present invention are used for insecticidal, acaricidal and/or nematicidal agents for agricultural and horticultural uses or for expellents of ticks parasitic on animals, they are generally mixed with appropriate carriers, for instance, solid carriers such as clay, talc, bentonite or diatomaceous earth, or liquid carriers such as water, alcohols (e.g., methanol and ethanol), aromatic hydrocarbons (e.g., benzene, toluene and xylene), chlorinated hydrocarbons, ethers, ketones, acid amides (e.g., dimethylformamide (DMF)) or esters (e.g., ethyl acetate). If desired, to these mixtures can be added a surfactant, eumulsifier, dispersing agent, suspending agent, penetrating agent, spreader, stabilizer and the like to put them into practical uses in the form of liquid preparation, smulsifiable concentration, wettable powder, dust, granule, flowable or the like. Moreover, the resulting mixtures may be incorporated with other herbicides, various insecticides, plant-growth regulating agents and/or synergists during preparation or application thereof, as necessary.

When the present compounds are used in the agricultural and horticultural fields, the amount to be applied as an active ingredient is in the range of 0.005 to 50 kg per hectare. It is more preferable to apply 0.01 to 5 kg/hectare.

When the present compounds are used for controlling ectoparasites on animals, in general, diluted aqueous solution of 2 to 50,000 ppm can be used as concentration of active ingredient, more preferably 10 to 1,000 ppm.

In the following, there are shown component ratios of formulations and formulation examples of insecticidal, acaricidal and/or nematicidal compositions and expellent compositions for ticks parasitic on animals, said compositions containing the compounds of the present invention as active ingredients. These examples are merely illustrative and not to restrict the invention. In the following examples, "part" means "part by weight" and "%" means "% by weight".

1. Components Ratio of Formulation

(1) Emulsifiable concentrates

    ______________________________________                                         Active ingredient:                                                                            5-25%                                                           liquid carrier:                                                                              52-90%    (Xylene, DMF, Methyl                                                           naphthalene, Cyclo-                                                            hexanone, Dichloro-                                                            benzene, Isophorone)                                   surface active agent:                                                                         5-20%    (Sorpol 2680,                                                                  Sorpol 3005X,                                                                  Sorpol 3346)                                           others:        0-20%    (Piperonyl butoxide:                                                           0-20%                                                                          Benzotriazole:                                                                 0-5%)                                                  ______________________________________                                    

(2) Oil solutions

    ______________________________________                                         Active ingredient:                                                                             5-30%                                                          liquid carrier:                                                                               70-95%     (Xylene, Methyl                                                                cellosolve,                                                                    Kerosene)                                            ______________________________________                                    

(3) Flowables

    ______________________________________                                         Active ingredient:                                                                            5-70%                                                           liquid carrier:                                                                             12.4-78.4% (water)                                                surface active agent:                                                                         1-10.5%      (Lunox 1000C,                                                                  Sorpol 3353,                                                                   Soprophor FL,                                                                  Nippol, Agrisol                                                                S-710, Lignin                                                                  sulfonic acid                                                                  soda)                                              others:        0-10%        Formalin 0-0.3%,                                                               Ethylene glycol                                                                0-10%, Propylene                                                               glycol 0-10%)                                      ______________________________________                                    

(4) Wettable powders (W.P.)

    ______________________________________                                         Active ingredient:                                                                             5-70%                                                          Solid carrier: 15-89%    (Calcium carbonate,                                                            Kaolinite, Zeeklite                                                            D, Zeeklite PFP,                                                               Diatomaceous earth,                                                            Talc)                                                 surface active agent:                                                                          3-10%    (Sorpol 5039, Lunox                                                            1000C, Sulfonic acid                                                           calcium, Sodium                                                                dodecyl-sulfonate,                                                             Sorpol 5050, Sorpol                                                            005D, Sorpol 5029-O)                                  ______________________________________                                    

(5) Dusts

    ______________________________________                                         Active ingredient:                                                                           0.01-30%                                                         solid carrier:                                                                                 67-99%  (Calcium carbonate,                                                            Kaolinite, Zeeklite,                                                           Talc)                                                  others:         0-3%    (Diisopropylphos-                                                              phate 0-1.5%,                                                                  Carplex #80: 0-3%)                                     ______________________________________                                    

(6) Granules

    ______________________________________                                         Active ingredient:                                                                            0.1-30%                                                         solid carrier:  67-99%   (Calcium carbonate,                                                            Kaolinite, Talc,                                                               Bentonite)                                            others:          0-8%    (Calcium lignin                                                                sulfonate: 0-3 wt %,                                                           Polyvinylalcohol:                                                              0-5%)                                                 ______________________________________                                    

2. Formulation Examples

Formulation Example 1: Emulsifiable concentrates

    ______________________________________                                         Active ingredient      20 parts                                                Xylene                 55 parts                                                N,N--dimethylformamide 20 parts                                                Solpol 2680 (trade name, a mixture of                                                                  5 parts                                                a non-ionic surface-active agent and                                           an anionic surface-active agent                                                manufactured by Toho Chemicals, Co.,                                           Ltd., Japan)                                                                   ______________________________________                                    

The above components are mixed intimately together to form an emulsifiable concentrate. Upon use, the emulsifiable concentrate is diluted with water up to one fiftieth to one twenty thousandth in concentration and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 2: Wettable powders

    ______________________________________                                         Active ingredient       25 parts                                               Zeeklite PFP (trade name, a mixture of                                                                 66 parts                                               kaolinite and sericite manufactured                                            by Zeeklite Mining Industries Co., Ltd.)                                       Solpol 5039             4 parts                                                (trade name, an anioic surface-active                                          agent manufactured by Toho Chemical                                            Co., Ltd., Japan)                                                              Carplex #80             3 parts                                                (trade name, white carbon manufactured                                         by Shionogi Seiyaku K.K., Japan)                                               Calcium lingin sulfonate                                                                               2 parts                                                ______________________________________                                    

The above components are homogeneously mixed together and ground to form a wettable powder. Upon use, the wettable powder is diluted with water up to one fiftieth to one twenty thousandth and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 3: Oil solutions

    ______________________________________                                         Active ingredient                                                                               10 parts                                                      methylcellosolve 90 parts                                                      ______________________________________                                    

The above components are homogeneously mixed together to form an oil solution. Upon use, the oil solution is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 4: Dusts

    ______________________________________                                         Active ingredient         3.0 parts                                            Carplex #80 (trade name, white carbon                                                                    0.5 parts                                            manufactured by Shionogi Seiyaku                                               K.K., Japan)                                                                   Clay                      95.0 parts                                           di-isopropyl phosphate    1.5 parts                                            ______________________________________                                    

The above components are homogeneously mixed together and ground to form a dust. Upon use, the dust is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 5: Granules

    ______________________________________                                         Active ingredient   5 parts                                                    Bentonite          54 parts                                                    Talc               40 parts                                                    Calcium lignin sulfonate                                                                           1 part                                                     ______________________________________                                    

The above components are mixed intimately together and ground, incorporated with a small amount of water and mixed together with stirring. The resulting mixture is granulated by means of extrusion-granulator and dried to form granules. Upon use, the granule is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 6: Flowables

    ______________________________________                                         Active ingredient        25 parts                                              Solpol 3353 (trade name, a nonionic                                                                     10 parts                                              surface-active agent manufactured                                              by Toho Chemical Co., Ltd., Japan)                                             Runox 1000C (trade name, an anionic                                                                     0.5 parts                                             surface-active agent manufactured                                              by Toho Chemical Co., Ltd., Japan)                                             1% aqueous solution of Xanthan gum                                                                      20 parts                                              (natural high-molecular compound)                                              Water                    44.5 parts                                            ______________________________________                                    

The above components except the active ingredient are homogeneously mixed together to form a solution, and thereto is added the active ingredient. The resulting mixture is throughly stirred, and wet-ground by means of sand mill to form a flowable. Upon use, the flowable is diluted up to one fiftieth to one twenty thousandth with water and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

The compounds according to the present invention not only exhibit superior insecticidal action on hemiptera insect such as green rice leafhopper (Nephotettix cincticeps), lepidoptera insect such as diamondback moth (Plutella xylostella), Coleoptera and sanitary insect pests such as pale house mosquito (Culex pipiens), but are also useful for expelling mites parasitic on fruits and vegetables, such as two-spotted spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Carmine mite (Tetranychus cinnabarinus), citrus red mite (Panonychus citri) and European red mite (Panonychus ulmi), as well as ticks parasitic on animals, such as southern cattle tick (Boophilus microplus), cattle tick (Boophilus annulatus), gulf coast tick (Amblyomma maculatum), brown-ear tick (Rhipicephalus appendiculaturs) and Haemaphysalis longicornis. The main features of the compounds of the present invention reside in that the compounds are useful for the prevention or control of blight (or disease) of fruits and vegetables, such as powdery mildew, downy mildew, rust, rice blast disease (or rice blight) etc. in addition to having the above mentioned insecticidal, acaricidal and nematicidal actions. Accordingly, the compounds of the present invention are an excellent agricultural drug which enables control of pests and blight (or disease) simultaneously. Moreover, they are excellent as an expellent for ticks parasitic on animals such as domestic animals (e.g. cattle, horse, sheep and pig), domestic fowls, and other animals such as dog, cat, rabbit and the like.

The present invention is further explained in detail by way of the following test example.

TEST EXAMPLE 1 Insecticidal test on Green rice leafhopper (Nephotettix cincticeps)

20% emulsifiable concentrate of each of the present compounds described in the specification (some of which were applied with 25% wettable powder) was diluted with water containing an extender to prepare a 1000 ppm aqueous emulsion. This aqueous emulsion was dispersed in full amount to stems and leaves of paddy planted in a pot of 1/20000 and air-dried. Twenty second instar green rice leafhopper larvae which would show resistance to organic phosphorus type insecticides or carbamate type insecticides, per pot, were released in the pots. The paddies were covered with a cylindrical wire gauge and then placed in a thermostatic chamber. The numbers of the larvae killed was determined after 96 hours and the mortality thereof was calculated according to the equation below. Incidentally, the test was repeated twice for each compound. ##EQU1##

As the results, the following compounds exhibited 100% of mortality.

    ______________________________________                                         Compound Nos.                                                                               14, 16, 17, 21, 22, 24, 25, 26, 29, 30, 31,                                    32, 33, 36, 38, 40, 41, 44, 45, 49, 53, 56,                                    61, 71, 72, 73, 75, 76, 77, 78, 79, 80, 82,                                    83, 84, 85, 87, 88, 89, 90, 92, 93, 97, 98,                                    99, 111, 112, 113, 127, 128, 129, 131, 148,                                    150, 174, 191, 202, 217, 220, 221, 226, 232,                                   235, 236, 239, 240, 267, 268, 269, 273, 277,                                   279, 280, 283, 284, 285, 288, 292, 323, 324,                                   359, 360, 364, 398, 426, 427, 429, 430, 432,                                   438, 443, 465, 466, 467, 468, 470, 472, 474,                                   475, 476, 477, 481, 482, 484, 488, 489, 490,                                   492, 494, 496, 498, 500, 514, 517, 518, 519,                                   520, 522, 524, 527, 528, 529, 540, 542, 565,                                   606, 609, 610, 643, 647, 652, 656, 657, 661,                                   664, 668, 670, 672, 676, 680, 702, 704, 708,                                   720, 722, 850, 851, 852, 857, 895, 1000,                                       1001, 1002 and 1143.                                              ______________________________________                                    

TEST EXAMPLE 2 Insecticidal test on 28-spotted Lady beetle (Henosepilachna vigintioctopunctata)

A leaf of tomato was immersed for about 10 seconds in a 1000 ppm aqueous emulsion which had been prepared by diluting a 20% emulsifiable concentrate containing each compound described in the present specification (some of which were applied with 25% wettable powder) with water containing an extender and then air-drying. The leaf thus treated was placed in a laboratory dish, into which 10 second inster 28-spotted lady beetle larvae were released. The dish was then fitted with a cap provided with pores and then placed in a thermostatic chamber kept at 25° C. The number of the larvae killed was determined after 96 hours and the mortality thereof was calculated according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

As the results, the following compounds exhibited 100% mortality.

    ______________________________________                                         Compound Nos.                                                                               13, 14, 16, 17, 18, 21, 24, 25, 26, 29,                                        30, 31, 32, 33, 34, 36, 38, 40, 41, 44,                                        45, 46, 49, 53, 55, 56, 70, 71, 72, 73,                                        74, 75, 76, 77, 78, 79, 80, 82, 83, 84,                                        85, 87, 88, 89, 90, 92, 93, 94, 95, 97,                                        99, 100, 111, 112, 113, 127, 128, 129,                                         131, 134, 150, 161, 174, 191, 192, 193,                                        194, 202, 216, 217, 218, 220, 221, 226,                                        232, 235, 236, 248, 250, 251, 268, 269,                                        279, 280, 283, 284, 285, 288, 290, 323,                                        324, 360, 426, 427, 429, 430, 432, 438,                                        443, 463, 465, 466, 467, 468, 470, 472,                                        474, 475, 476, 477, 480, 481, 482, 484,                                        488, 489, 490, 492, 494, 496, 498, 500,                                        514, 517, 518, 519, 520, 522, 524, 527,                                        528, 529, 540, 542, 609, 618, 643, 652,                                        657, 662, 664, 668, 702, 704, 722, 843,                                        850, 851, 852, 857, 863, 895, 1002, 1141                                       and 1143.                                                         ______________________________________                                    

TEST EXAMPLE 3 Acaricidal test on Kanzawa Spider Mite (T. kanzawai)

A leaf of kidney bean was cut into a round piece of 1.5 cm in diameter by a leaf punch, and then placed on a moistened filter paper on a polystyrol cup of 7 cm in a diameter. Each piece of the leaf was inoculated with 10 Kanzawa Spider Mite nymphs. Half a day after the inoculation, each 2 ml of an aqueous emulsion containing 1000 ppm of the present compuond described in the speciication (some of which were applied with 25% wettable powder) diluted with water containing an extender was applied to each polystyrol cup by means of a rotary spray tower. After 96 hours, the mortality of the nymph was determined according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

As the results, the following compounds exhibited 100% mortality.

    ______________________________________                                         Compound Nos.                                                                               13, 14, 15, 16, 17, 18, 24, 25, 26, 28,                                        29, 30, 31, 32, 33, 36, 40, 41, 44, 45,                                        49, 53, 55, 56, 70, 74, 76, 77, 78, 80,                                        83, 84, 85, 87, 88, 89, 90, 92, 93, 95,                                        97, 98, 99, 100, 111, 112, 113, 120, 129,                                      148, 150, 152, 161, 174, 191, 193, 194,                                        195, 197, 220, 221, 224, 226, 232, 235,                                        236, 240, 241, 250, 283, 287, 288, 290,                                        324, 344, 359, 360, 364, 398, 410, 421,                                        426, 427, 429, 430, 432, 438, 443, 463,                                        466, 467, 468, 470, 472, 475, 476, 477,                                        480, 481, 482, 488, 489, 490, 494, 514,                                        517, 518, 519, 520, 527, 529, 542, 606,                                        609, 610, 612, 643, 702, 704, 708, 720,                                        850, 851, 852, 857, 863, 895, 1001, 1002                                       and 1142.                                                         ______________________________________                                    

TEST EXAMPLE 4 Nematicidal test on Root-knot Nematode (Meloidogyne sp.)

Soil contaminated with root-knot nematode was placed in a polystyrol cup 8 cm in diameter. A liquid containing 1000 ppm of an active ingredient was prepared by diluting 20% emulsifiable concentrate containing a compound of the present invention (some of which were applied with 25% wettable powder) with water containing an extender. The soil contaminated with nematode and placed in the polystyrol cup was drenched with each 50 ml of the resulting liquid. After 48 hours, a tomato seedling as an indicator was transplanted into the soil thus treated. Thirty days after the transplanation, the roots of the tomato were washed with water and the root-knot parasitism was checked by observation. Incidentally, the test was repeated twice for each compound. As a result, no root-knot parasitism was observed in the roots of the tomato treated with the exhibit a strong nematicidal activity:

    ______________________________________                                         Compound Nos.                                                                               17, 72, 73, 76, 78, 84, 85, 90, 92, 93,                                        221, 268, 269, 280, 283, 359, and 465.                            ______________________________________                                    

TEST EXAMPLE 5 Insecticidal test on Green rice leafhopper (Nephotettix cincticeps)(Comparative test)

Test was conducted in accordance with Test Example 1 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compounds exhibit much higher insecticidal activity than the known control compounds.

TEST EXAMPLE 6 Insectical test on 28-spotted Lady Beetle (Henosepilachna vigintioctopunctata)(Comparative test)

Test was conducted in accordance with Test Example 2 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compunds exhibit much higher insecticidal activity then the known control compounds.

TEST EXAMPLE 7 Acaricidal test on Kanzawa Spider Mite (T. kanzawai)(Comparative test)

Test was conducted in accordance with Test Example 3 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compounds exhibit much higher acaricidal activity than the known control compounds.

                  TABLE 5                                                          ______________________________________                                         Insecticidal Test (Comparative test)                                                      Green rice 28-spotted lady                                                                            Kanzawa                                                 leafhopper beetle      spider mite                                  Compound No.                                                                              (mortality %)                                                                             (mortality %)                                                                              (mortality %)                                ______________________________________                                         Present compound                                                                          100        100         100                                          No. 40                                                                         Present compound                                                                          100        100         100                                          No. 92                                                                         Present compound                                                                          100        100         100                                          No. 465                                                                        Control    0          20          0                                            compound A                                                                     Control    20         0           50                                           compound B                                                                     ______________________________________                                    

The structural formulae of the present compounds in Table 5 are as follows: ##STR17##

On the other hand, the structural formulae of the control compounds are as follows: ##STR18##

TEST EXAMPLE 8 Residual activity text on 28-spotted lady beetle (Henosepilachna vigintioctopunctata)

Tomato planted in a pot of 1/5000 are was sprayed well with a 500 ppm aqueous emulsion which had been prepared by diluting with water containing an extender 20% emulsifiable concentrate containing each compound described in the present specification (some of which were applied with 25% wettable powder), air-dried and kept in a greenhouse. After 10 days, leaf of the tomato thus treated was cut out and placed in a laboratory dish, into which 10 second inster 28-spotted lady beetle larvae were released. The dish was then fitted with a cap provided with pores and then placed in a thermostatic chamber kept at 25° C. The number of the larvae killed was checked after 96 hours and the mortality thereof was calculated according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

The following compounds exhibited 100% mortality.

    ______________________________________                                         Compound Nos.                                                                               22, 84, 85, 89, 90, 112, 113, 426, 427,                                        429, 430, 432, 438, 443, 465, 468, 470,                                        472, 481, 490, 496, 517, 520, 522, 528,                                        857 and 895.                                                      ______________________________________                                     

What is claimed is:
 1. A compound of the following formula: ##STR19## wherein Z³ represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR20## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is O or an integer of 1 to 2, and when m is 2, W may be same or different.
 2. A composition for controlling insects, acari and nemati for argricultural and horticultural use and containing as active ingredient a compound of the following formula: ##STR21## wherein Z³ represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR22## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is O or an integer of 1 to 2, and when m is 2, W may be same or different.
 3. A 2-t-butyl-4-chloro-5-[2-2,6-dimethyl-4-(4-methylphenoxy)phenoxy ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR23##
 4. A 2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-phenoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR24##
 5. A 2-t-butyl-4-chloro-5-[2-{2,6-dimethyl-4-(2,4-difluorobenzoyl)phenoxy}ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR25##
 6. A 2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-ethoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR26##
 7. A 2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-methoxymethyl-phenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR27## 